光响应聚合物胶束结构稳定性及其光控酸敏行为
|
摘要
光响应聚合物广泛应用于形状记忆材料、智能传感和药物缓控释等领域。探索光响应聚合物光化学反应的状态依赖性，具有重要的学术意义和应用价值。在系统文献调研的基础上，本论文以PEMSD为大分子链转移剂，采用可见光活化室温RAFT聚合法精确制备了一系列分子量分布窄、以生色基团肉桂基直接键接环缩醛的具有光和pH双重响应的聚(5-乙基-5-甲基丙烯酰氧甲基-2-苯乙烯基-[1,3]二氧环己烷)-b-聚(聚乙二醇单甲醚甲基丙烯酸)(PEMSD-b-PPEGMA)两亲嵌段共聚物。采用~1H NMR、FTIR等方法，研究了PEMSD链在均相溶液和胶束纳米限域本体状态下的光化学反应特征。在此基础上，探索利用肉桂基在均相溶液和胶束纳米限域的本体状态下的光化学反应特征，调控聚合物环缩醛键的水解速度，进而实现胶束酸敏行为的光调控。研究结果表明，在乙腈中PEMSD_(52)-b-PPEGMA_(40)能组装形成规整的球形胶束，有效地对PEMSD链进行纳米限域。PEMSD链肉桂基的光化学反应具有状态选择性，在均相溶液中只发生光致异构；在胶束核纳米限域的本体状态只发生光致[2+2]环加成，导致胶束核PEMSD链光致交联。胶束核中，PEMSD链的水解速度受控于肉桂基的先期顺式异构程度。异构程度越大，胶束水解速度越慢。紫外光照胶束3min足以稳定胶束，但不改变胶束的水解速度，光照30min则显著降低胶束的水解速度。由此推断，通过肉桂基先期光致异构，进一步在胶束核中光致交联，可宽范围调控胶束的酸敏行为。本论文为光调控水溶性高分子提供了新思路，在药物缓控释等领域具有重要的应用前景。
Photo-responsive polymers were widely used for shape memory materials, intelligentsensor, drug controlled-release and other fields. It is important in academic andapplication to explore the state dependence of photo-chemical reaction. Based on thedetailed literature research, this thesis describes the structurally stable and acid-sensitivemicelles whose stability and acid sensitivity can be widely tuned simply via a batch UVirradiation. To this end, the well-defined poly(5-ethyl-5-methacryloyloxymethyl-2-styryl-[1,3]dioxane)-block-poly[poly(ethylene glycol) monomethyl ether methacrylate](PEMSD-b-PPEGMA) copolymers with identical chain lengths of PEMSD blocks at DP=52but different chain lengths of PPEGMA blocks were synthesized via RAFTpolymerization under mild visible light radiation at30oC. The results demonstrated thatirradiating the homogeneous acetone solution solely induced Z-isomerization, withoutdetectable dimerization of cinnamyl groups. This Z-isomerization did not affect theformation of regular and spherical core-shell micelles of PEMSD_(52)-b-PPEGMA_(40)inacetonitrile. However, irradiating the bulky PEMSD chains of100%E-cinnamylPEMSD_(52)-b-PPEGMA_(40)in nanoscale-confined micellar cores solely induced thedimerization without detectable Z-isomerization. Z-isomerization remarkably improvedthe acid stability of the bulky PEMSD chains in micellar cores. Irradiating theZ-isomerized micelles for3min led to the structural stabilization but without changingthe acid sensitivity; while irradiating for30min remarkably improved the acid stabilityof the micelles. It can be concluded, the acid-sensitivity of micelles can be widely tunedby the dimerization of bulky Z-isomerized PEMSD chains in micellar cores. This thesisprovides a new avenue toward photo-controlled water soluable polymer. It shows greatapplication potential in drug controlled-release.
Photo-responsive polymers were widely used for shape memory materials, intelligentsensor, drug controlled-release and other fields. It is important in academic andapplication to explore the state dependence of photo-chemical reaction. Based on thedetailed literature research, this thesis describes the structurally stable and acid-sensitivemicelles whose stability and acid sensitivity can be widely tuned simply via a batch UVirradiation. To this end, the well-defined poly(5-ethyl-5-methacryloyloxymethyl-2-styryl-[1,3]dioxane)-block-poly[poly(ethylene glycol) monomethyl ether methacrylate](PEMSD-b-PPEGMA) copolymers with identical chain lengths of PEMSD blocks at DP=52but different chain lengths of PPEGMA blocks were synthesized via RAFTpolymerization under mild visible light radiation at30oC. The results demonstrated thatirradiating the homogeneous acetone solution solely induced Z-isomerization, withoutdetectable dimerization of cinnamyl groups. This Z-isomerization did not affect theformation of regular and spherical core-shell micelles of PEMSD_(52)-b-PPEGMA_(40)inacetonitrile. However, irradiating the bulky PEMSD chains of100%E-cinnamylPEMSD_(52)-b-PPEGMA_(40)in nanoscale-confined micellar cores solely induced thedimerization without detectable Z-isomerization. Z-isomerization remarkably improvedthe acid stability of the bulky PEMSD chains in micellar cores. Irradiating theZ-isomerized micelles for3min led to the structural stabilization but without changingthe acid sensitivity; while irradiating for30min remarkably improved the acid stabilityof the micelles. It can be concluded, the acid-sensitivity of micelles can be widely tunedby the dimerization of bulky Z-isomerized PEMSD chains in micellar cores. This thesisprovides a new avenue toward photo-controlled water soluable polymer. It shows greatapplication potential in drug controlled-release.
引文
1Tomatsu I.; Peng K.; Kros A. Photoresponsive hydrogels for biomedical applications [J]. Adv.DrugDeliv.Rev.2011,63:1257-1266.
2Zhao Y. Photocontrollable Block Copolymer Micelles: What Can We Control [J]. J. Mater. Chem.2009,19:4887-4895.
3Shimoboji T.; Larenas E.; Fowler T.; Kulkarni S.; Hoffman A. S.; Stayton P. S. PhotoresponsivePolymer-Enzyme Switches [J]. Proc. Natl. Acad. Sci USA2002,99:16592-16596.
4Ruhmann R. Polymers for Optical Storage-hotoresponsive Polymers by Structure Variation inSide-Group Polymethacrylates [J]. Polym. Int.1997,43:103-108.
5He J.; Tong X.; Zhao Y. Photoresponsive Nanogels Based on Photocontrollable Cross-linkings [J].Macromolecules.2009,42:4845-4852.
6Moniruzzaman M.; Sabey C. J.; Fernando G. F. Photoresponsive Polymers: An Investigation ofTheir Photoinduced Temperature Changes during Photoviscosity Measurements [J]. Polymer.2007,48:255-263.
7Alonso M.; Reboto V.; Guiscardo L.; San M. A.; Rodriguez J. C. Spiropyran Derivative of AnElastin-Like Bioelastic Polymer: Photoresponesive Molecule Machine to Covert Sunlight intoMechanical Work [J]. Macromolecules.2000,33:9480-9482.
8Nagasaki T. Photoresponsive Polymeric Materials for Drug Delivery Systems: Double Targetingwith Photoresponsive Polymers [J]. Drug Delivery Syst.2008,23:637-643.
9Tong X.; Wang G.; Soldera A.; Zhao Y. How Can Azobenzene Block Copolymer Vesicles beDissociated and Reformed by Light?[J]. J. Phys. Chem. B.2005,109:20281-20287.
10Wang G.; Tong X.; Zhao Y. Preparation of Azobenzene-Containing Amphiphilic DiblockCo-polymers for Light-Responsive Micellar Aggregates [J]. Macromolecules2004,37:8911-8917.
11Lin L.; Yan Z.; Gu J.; Zhang Y.; Feng Z.; Yu Y. UV-Responsive Behavior ofAzopyridine-Containing Diblock CopolymericVesicles: Photoinduced Fusion, Disintegration andRearrangement [J]. Macromol. Rapid Commun.2009,30:1089-1093.
12Puntoriero F.; Ceroni P.; Balzani V.; Bergamini G.; V gtle F. Photoswitchable Dendritic Hosts: ADendrimer with Peripheral Azobenzene Groups [J]. J. Am. Chem. Soc.2007,129:10714-10719.
13Yamada M.; Kondo M.; Mamiya J.; Yu Y.; Kinoshita M.; Barrett C. J.; Ikeda T. PhotomobilePolymer Materials: Towards Light-Driven Plastic Motors [J]. Angew. Chem. Int. Ed.2008,47:4986-4988.
14Berkovic G.; Krongauz V.; Weiss V. Spiropyrans and Spirooxazines for Memories and Switches[J]. Chem. Rev.2000,100:1741-1754.
15Sanchez C.; Lebeau B.; Chaput F.; Boilot J. P. Optical Properties of Functional HybridOrganic–Inorganic Nanocomposites [J]. Adv. Mater.2003,15:1969-1994.
16Guo X.; Zhang D.; Zhou Y.; Zhu D. Synthesis and Spectral Investigations of a New Dyad withSpiropyran and Fluorescein Units: Toward Information Processing at the Single Molecular Level[J]. J. Org. Chem.2003,68:5681-5687.
17Mazzi L.D.; Eugenii K.; Itamar W. Amperometric transdusion of optical signals recorded byorganized monolayers of photoisomerizable spiropyran [J]. J.Am.Chem.Soc.1994,116:7413-7414.
18Parthenopoulos D. A.; Rentzepis P. M. Three-dimensional optical storage memory [J]. Science1989,245:843-845.
19Ito Y.; Sugimura N.; Kwon O. H.; Imanishi Y. Enzyme modification by polymers with solubilitiesthat change in response to photoirradiation in organic media [J]. Nat. Biotechnol.1999,17:73-75.
20Kocer A.; Walko M.; Meijberg W.; Ben L. F. A light-activated nanovalve derived from a channelprotein [J]. Science.2005,309:755-758.
21Vlassiouk I.; Park C. D.; Vail S. A.; Gust D.; Smirnov S. Control of Nanopore Wetting by aPhotochromic Spiropyran: A Light-Controlled Valve and Electrical Switch [J]. Nano Lett,2006,6:1013-1017.
22Lee H.; Wu W.; Oh J. K.; Mueller L.; Sherwood G.; Peteanu L.; Kowalewski T.; Matyjasz-ewskiK. Light-Induced Reversible Formation of Polymeric Micelles [J]. Angew. Chem. Int. Ed.2007,46:2453-2457.
23Chen J.; Zeng F.; Wu S.; Zhao J.; Chen Q.; Tong Z. Reversible fluorescence modulation throughenergy transfer with ABC triblock copolymer micelles asscaffoldsw [J]. Chem. Commun.2008,5580-5582.
24Chen J.; Zeng F.; Wu S.; Chen Q.; Tong Z. A Core-Shell Nanoparticle Approach toPhoto-reversible Fluorescence Modulation of a Hydrophobic Dye in AqueousMedia [J]. Chem.Eur. J.2008,14,4851-4860.
25Jin Q.; Liu G.; Ji J. Micelles and Reverse Micelles with a Photo and Themo Double-ResponsiveBlock Copolymer [J]. J. Polym. Sci: Part A: Polym. Chem.2010,48:2855-2861.
26Jiang J.; Tong X.; Morris D.; Zhao Y. Toward Photocontrolled Release Using Light-DissociableBlock Copolymer Micelles [J]. Macromolecules2006,39:4633-4640.
27Vivero-Escoto J.; Slowing I.; Wu C.; and Lin V. S.-Y. Photoinduced Intracellular ControlledRelease Drug Delivery in Human Cells by Gold-Capped Mesoporous Silica Nanosphere [J]. J. Am.Chem. Soc.2009,131:3462-3463.
28Babin J.; Pelletier M.; Lepage M.; Allard J.F.; Morris D.; Zhao Y. A New Two-Photon-SensitiveBlock Copolymer Nanocarrier [J]. Angew. Chem. Int. Ed.2009,48:3329-3332.
29Jiang J.; Tong X.; Zhao Y. A New Design for Light-Breakable Polymer Micelles [J]. J. Am. Chem.Soc.2005,127:8290-8291.
30Jiang X.; Lavender C. A.; Woodcock J. W.; Zhao B. Multiple Micellization and DissociationTransitions of Thermo-and Light-Sensitive Poly(ethylene oxide)-b-poly(ethoxytri(ethylene glycol)acrylate-co-o-nitrobenzyl acrylate) in Water [J]. Macromolecules.2008,41:2632-2643.
31Jiang X.; Jin S.; Zhong Q.; Dadmun M. D.; Zhao B. Stimuli-Induced Multiple Sol-Gel-SolTransitions of Aqueous Solution of a Thermo-and Light-Sensitive Hydrophilic Block Co-polymer[J]. Macromolecules.2009,42:8468-8476.
32Lai J.; Mu X.; Xu Y.; Wu X.; Wu Ch.; Li C.; Chen J.; Zhao Y.; Light-responsive nanogatedensemble based on polymer grafted mesoporous silica hybrid nanoparticles [J]. Chem. Commun.2010,46:7370-7372.
33Ionov L.; Diez S. Environment-Friendly Photolithography UsingPoly(N-isopropylacrylamide)-Based Thermoresponsive Photoresists [J]. J. Am. Chem. Soc.2009,131:13315-13319.
34Ding J.; Liu G. Polystyrene-block-poly(2-cinnamoylethyl methacrylate)Nanospheres withCross-Linked Shells [J]. Macromolecules.1998,31:6554-6558.
35Jiang J.; Qi B.; Lepage M.; Zhao Y. Polymer Micelles Stabilization on Demand throughReversible Photo-Cross-Linking [J]. Macromolecules.2007,40:790-792.
36Sinkel C.; Greiner A.; Agarwal S. Synthesis, Characterization, and Properties Evaluation ofMethylcoumarin End-Functionalized Poly(methyl methacrylate) for Photoinduced Drug Release[J]. Macromolecules.2008,41:3460-3467.
37Iliopoulos K.; Krupka O.; Gindre D.; SalléM. Reversible Two-Photon Optical Data Storage inCoumarin-Based Copolymers [J]. J. Am. Chem. Soc.2010,132,14343-14345.
38Kirmse.W.100Years of the Wolff Rearrangement [J]. Eur. J. Org. Chem.2002,14:2193-2256.
39(a) Almstead, J. I. K.; Urwyler B.; Wirz, J. Flash Photolysis of a-Diazonaphthoquinones inAqueous Solution: Determination of Rates and Equilibria for Keto-Enol Tautomerization of1-Indene-3-carboxylic Acid [J]. J. Am. Chem. Soc.1994,116,954-960.
40Goodwin A. P.; Mynar J. L.; Ma Y.; Fleming G. R.; Fréchet J. M. J. Synthetic Micelle Sensitive toIR Light via a Two-Photon Process [J]. J. Am. Chem. Soc.2005,127:9952-9953.
41Mynar J. L.; Goodwin A. P.; Cohen J. A.; Ma Y.; Fleming G. R.; Fréchet J. M. J. Two-photondegradable supramolecular assemblies of linear-dendritic Copolymers [J]. Chem. Commun.2007,12:2081-2082.
42Horie K.; Mita I. Photoisomerization of Ethyl Cinnamate in Dilute Solutions [J]. J. Photochem.1934,26:185-192.
43Pattanaargson S.; Munhapol T.; Hirunsupachot P.; Luangthongaram P. Photoisomerization of octylmethoxycinnamate [J]. J of Photochem and Photobio A:Chemistry.2004,161:269-274.
44Ishigami T.; Nakazato K.; Uehara M.; Endo T. Marked Dependence of Multiplicity in Direct Z,EPhotoisomerization of a Series of Methyl Cinnamates on Their p-substituents [J]. Tetrahedron Lett.1979,20:863-866.
45Ketner A. M..; Kumar R.; Davies T; S.; Elder P. W.; Raghavan S. R. A Simple Class ofPhotorheological Fluids: Surfactant Solutions with Viscosity Tunable by Light [J]. J. Am. Chem.Soc.2007,129:1553-1559.
46Wijtmans M.; Rosenthal S. J.; Zwanenburg B.; Porter N. A. Visible Light Excitation of CdSeNanocrystals Triggers the Release of Coumarin from Cinnamate Surface Ligands [J]. J. Am. Chem.Soc.2006,128:11720-11726.
47Noyce D. S.; King P. A.; Kirby F. B.; Reed W. L. The Kinetics of the Acid-catalyzedIsomerization of cis-Cinnamic acid [J]. J. Am. Chem. Soc.1962,84:1632-1635.
48Reed G. A.; Dimmel D. R.; and Malcolm E. W. Influence of Nucleophiles on the HighTemperature Aqueous Isomerization of cis-to trans-Cinnamic Acid [J]. J. Org. Chem.1993,58:6364-6371.
49Shindo Y.; Horie K.; Mita I. Rate for Photodimerization of Ethyl Cinnmate in Diluted solution [J].Chem. Lett.1983,18,639-642.
50Shen S.; Torkelson J. M.; Elbed J. E.; Lewis F. D. Thermally irreversible photoresponsivepolymers:Synthesis and preliminary characterization of copolymers containing side-chaintrans-cinnamamide chromophores [J]. Macromol.Chem.phys.1990,191:2367-2375.
51Laschewsky A.; Reka E. D. Photochemical modification of the lower critical solution temperatureof cinnamoylated poly(N-2-hydroxypropylmethacrylamide) in water [J]. Macromol. Rapid.Commun.2000,21:937-940.
52Kawatsuki N.; Yamashita A.; Fujii Y.; Kitamura C.; Yoneda A. Thermally EnhancedPhotoinduced Reorientation in Photo-Cross-Linkable Liquid Crystalline Polymers Comprised ofCinnamate and Tolane Mesogenic Groups [J]. Macromolecules2008,41:9715-9721.
53Liu G.; Hu N.; Xu X.; Yao H. Cross-Linked Polymer Brushes.1. Synthesis of Poly[β-(vinylox y)ethyl cinnamate]-b-poly (isobutyl vinyl ether)[J]. Macromolecules1994,27:3892-3895.
54Guo A.; Liu G.; Tao J. Star Polymers and Nanospheres from Cross-Linkable Diblock Copolymers[J]. Macromolecules.1996,29:2487-2493.
55Tao J.; Stewart S.; Liu G.; Yang M.; Star and Cylindrical Micelles ofPolystyrene-block-poly(2-cinnamoylethyl methacrylate) in Cyclopentane [J]. Macromolecules.1997,30:2738-2745.
56Ding J.; Liu G. Polystyrene-block-poly(2-cinnamoylethyl methacrylate) Nanospheres withCross-Linked Shells [J]. Macromolecules.1998,31:6554-6558.
57Henselwood F.; Liu G. Water-Soluble Nanospheres of Poly(2-cinnamoylethylmethacrylate)-block-poly(acrylic acid)[J].Macromolecules.1997,30:488-493.
58Liu G.; Ding J.; Guo A.; Herfort M.; Bazett-Jones D. Potential Skin Layers for Membranes withTunable Nanochannels [J]. Macromolecules.1997,30,1851-1853.
59Tao J.; Liu G. Polystyrene-block-poly(2-cinnamoylethyl methacrylate) Tadpole Molecules [J].Macromolecules.1997,30:2408-2411.
60Kim J. S.; Jeon H. J.; Park J. J.; Park M. S.; Youk J. H. Encapsulation of Nanomaterials Using anIntermediary Layer Cross-Linkable ABC Triblock Copolymer [J]. J. Polym. Scie: Part A: PolymChem.2009,47:4963-4970.
61John B. M.; Robert H. G. Synthesis of Fluorine-18Functionalized Nanoparticles for use as invivo，Molecular Imaging Agents [J]. J. Am. Chem. Soc.2008,130:6731-6733.
62Jiang X.; Luo S.; Armes S. P.; Shi W.; Liu S. UV Irradiation-Induced Shell Cross-Linked Micelleswith pH-Responsiv e Cores Using ABC Triblock Copolymers [J]. Macromolecules.2006,39:5987-5994.
63Yusa S.; Sugahara M.; Endo T.; Morishima Y. Preparation and Characterization of apH-Responsive Nanogel Based on a Photo-Cross-Linked Micelle Formed From BlockCopolymers with Controlled Structure [J]. Langmuir.2009,25:5258-5265.
64Szczubialka K.; Moczek.; Blaszkiewicz S.; Nowakowska M. Photocrosslinkable SmartTerpolymers Responding to pH Temperature, and Ionic Strength [J]. J. Polym. Scie: Part A:Polym Chem.2004,42:3879-3886.
65Yuan X.; Fischer K.; Sch rtl W. Photocleavable Microcapsules Built from PhotoreactiveNanospheres [J]. Langmuir.2005,21:9374-9380.
66Yuan X.; Fischer K.; Sch rtl W. Reversible Cluster Formation of Colloidal Nanospheres byInterparticle Photodimerization [J]. Adv Funct.Mater.2004,14:457-463.
67Shi D.; Matsusaki M.; Kaneko T.; Akashi M. Photo-Cross-Linking and Cleavage InducedReversible Size Change of Bio-Based Nanoparticles [J]. Macromolecules.2008,41:8167-8172.
68Shi D.; Matsusaki M.; Akashi M. Photo-Cross-Linking Induces Size Change and StealthProperties of Water-Dispersible Cinnamic Acid Derivative Nanoparticles [J]. Bioconjugate Chem.2009,20:1917-1923.
69Chien L-C.; Cada L G. Photo-Cross-Linkable and Optically Active Side-Chain Liquid-CrystallineCopolymers [J]. Macromolecules.1994,27:3721-3726.
70Kawatsuki N.; Matsuyoshi K.; Hayashi M.; Takatsuka H.; Yamamoto T. Photoreaction ofPhoto-cross-linkable Methacrylate Polymer Films Comprising2-CinnamoyloxyethoxybiphenylSide Group by Linearly Polarized Ultraviolet Light and Liquid Crystal Alignment on the ResultantFilms [J]. Chem. Mater.2000,12:1549-1555.
71Furumi S.; Ichimura K. Surface-Assisted Photoalignment of Discotic Liquid Crystals byNonpolarized Light Irradiation of Photo-Cross-Linkable Polymer Thin Films [J]. J. Phys. Chem. B.2007,111:1277-1287.
72Chen W.; Meng F.; Li F.; Ji S.; Zhong Z. pH-Responsive Biodegradable Micelles Based onAcid-Labile,Polycarbonate Hydrophobe: Synthesis and Triggered Drug Release [J].Biomacromolecules.2009,10:1727-1735.
73Gillies E. R.; Fréchet J. M. J. A new approach towards acid sensitive copolymer micelles for drugdelivery [J]. Chem. Commun.2003,12:1640-1641.
74Griset A. P.; Walpole J.; Liu R.; Gaffey A.; Colson Y. L.;Grinstaff M. W. Expansile Nanoparticles:Synthesis, Characterization, and in Vivo Efficacy of an Acid-Responsive Polymeric Drug DeliverySystem [J]. J. Am. Chem. Soc.2009,131:2469-2471.
75Chen D.; Li N.; Gu H.; Xia X.; Xu Q.; Ge J.; Lu J.; Li Y. A novel degradable polymeric carrier forselective release and imaging of magnetic nanoparticles [J]. Chem. Commun.2010,46:6708-6710.
76Gillies E. R.; Jonsson T. B.; Fréchet J. M. J. Stimuli-Responsive Supramolecular Assemblies ofLinear-Dendritic Copolymers [J]. J. Am. Chem.Soc.2004,126:11936-11943.
77Morinaga H.; Morikawa H.; Wang Y.; Sudo A.; Endo T. Amphiphilic Copolymer HavingAcid-Labile Acetal in the Side Chain as a Hydrophobe: Controlled Release of Aldehyde byThermoresponsive Aggregation-Dissociation of Polymer Micelles [J]. Macromolecules.2009,42,2229-2235.
78Shi D.; Matsusaki M.; Akashi M. Photo-tunable protein release from biodegradable nanoparticlescomposed of cinnamic acid derivatives [J]. Journal of Controlled Release.2011,149:182-189.
79Ding J.; Zhuang X.; Xiao C.; Cheng Y.; Zhao L.; He C.; Tang Z.; Chen X. Preparation ofphoto-cross-linked pH-responsive polypeptide nanogels as potential carriers for controlled drugdelivery [J]. J. Mater. Chem.2011,21:11383-11391.
80Schumers J.-M.; Fustin C.-A.; Gohy J.-F. Light-Responsive Block Copolymers [J]. MacromolRapid Commun.2010,31:1588-1607.
81Peris S.; Tylkowski B.; Ronda J. C.; Garcia-Valls R.; Reina J. A.; Giamberini M. Synthesis,Characterization, and Photoresponsive Behavior of New Azobenzene-Containing Polyethers [J]. JPolym Sci, Part A: Polym Chem.2009,47:5426-5436.
82Lin L.; Yan Z.; Gu J.; Zhang Y.; Feng Z.; Yu Y. UV-Responsive Behavior ofAzopyridine-Containing Diblock Copolymeric Vesicles: Photoinduced Fusion, Disintegration andRearrangement [J]. Macromol Rapid Commun.2009,30:1089-1093.
83Yoshida T.; Kanaoka S.; Aoshima S. Living Cationic Polymerization of Azobenzene-ContainingVinyl Ether and Its Photoresponsive Behavior [J]. J. Polym Sci.Part A: Polym Chem.2005,43:5138-5146.
84Yu B.; Jiang X.; Wang R.; Yin J. Multistimuli Responsive Polymer Nanoparticles On the basis ofthe Amphiphilic Azobenzene-Contained Hyperbranched Poly(ether amine)(hPEA-AZO)[J].Macromolecules.2010,43:10457-10465.
85Ling J.; Rong M.; Zhang M. Coumarin imparts repeated photochemical remendability topolyurethan [J]. J. Mater Chem.2011,21:18373-18380.
86Zhao, Y.; Bertrand, J.; Tong, X.; Zhao, Y. Photo-Cross-Linkable Polymer Micelles inHydrogen-Bonding-Built Layer-by-Layer Films [J]. Langmuir.2009,25:13151-13157.
87He J.; Tong X.; Tremblay L.; Zhao, Y. Corona-Cross-Linked Polymer Vesicles Displaying aLarge and Reversible Temperature-Responsive Volume Transition [J]. Macromolecules.2009,42:7267-7270.
88Palczewski K.; Kumasaka T.; Hori T.; Behnke C. A.; Motoshima H.; Fox B. A.; Trong I. L.;Teller,D. C.; Okada T.; Stenkamp R. E.; Yamamoto M.; Miyano M. Crystal structure of rhodopsin: A Gprotein-coupled receptor [J]. Science.2000,289:739-745.
89Li Y.; Tang Y.; Yang K.; Chen X.; Lu L.; Cai Y. Facile Synthesis and Photo-Tunable Properties ofa Photosensitive Polymer Whose Chromophores Bound with pH-Labile Cyclic Acetal Linkages [J].Macromolecules.2008,41:4597-4606.
90Liu Z.; Tang Y.; Li N.; Lu L.; Deng J.; Cai Y. Modulating light-tunable acid sensitivity of abioinspired polymer simply by adjusting the position of a single methoxy substituent [J]. J. Polym.Sci.: Part A: Polym. Chem.2012,50:495-508.
91Lu L.; Zhang H.; Yang N; Cai Y. Toward Rapid and Well-Controlled Ambient TemperatureRAFT Polymerization under UV-Vis Radiation: Effect of Radiation Wave Range [J].Macromolecules.2006,39:3770-3776.
92Sun J.; Peng Y.; Chen Y.; Liu Y.; Deng J.; Lu L.; Cai Y. Effect of Molecular Structure onThermoresponsive Behaviors of Pyrrolidone-Based Water-Soluble Polymers [J]. Macromolecules.2010,43:4041-4049.
93Deng J.; Shi Y.; Jiang W.; Peng Y.; Lu L.; Cai Y. Facile Synthesis and ThermoresponsiveBehaviors of a Well-Defined Pyrrolidone Based Hydrophilic Polymer [J]. Macromolecules.2008,41:3007-3014.
94Boiko N.; Zhu X.; Bobrovsky A.; Shibaev V. First Photosensitive Liquid CrystallineDendrimer:Synthesis, Phase Behavior, and Photochemical Properties [J]. Chem. Mater.2001,13:1447-1452.
95Coqueret X. Photoreactivity of polymers with dimerizable side-groups: Kinetic analysis forprobing morphology and molecular organization [J]. Macromol. Chem. Phys.1999,200:1567-1579.
96Xu F. J.; Li Y. L.; Kang E. T.; Neoh K. G. Heparin-coupled poly(poly(ethyleneglycol)monomethacrylate)-Si(III) hybrids and their blood compatible surfaces [J].Biomacromolecules.2005,6:1759-1768.
97Tao L.; Mantovani G.; Lecolley F.; Haddleton D. M.-Aldehyde terminally functionalmethacrylic polymers from living radical polymerization: application in proteinconjugation"Pegylation"[J]. J. Am. Chem. Soc.2004,126:13220-13221.
98Walter J. M.; Greenfield D.; Bustamante C.; Liphardt J. Light-powering escherichia coli withproteorhodopsin [J]. Proc. Natl. Acad. Sci. U. S. A.2007,104:2408-2412; Schulten K.; Tavan P. A.mechanism for the light-driven proton pump of Halobacterium halobium [J]. Nature1978,272:85-86; Hampp N. Bacteriorhodopsin as a photochromic retinal protein for optical memories [J].Chem. Rev.2000,100:1755-1776.
99Chen R. L.; Liu R. S. H. New hindered isomers of3-dehydroretinal (vitamin A2)[J]. Tetrahedron.1996,52:7809-7816.
100Dugave C.; Demange L. Cis-Trans isomerization of organic molecules andbiomolecules:Implications and Applications [J]. Chem. Rev.2003,103:2475-2532.
101Pfoertner K. H. Novel photosensitizers for the E/Z-isomerization of trienes. Part1.syntheses andapplication [J]. J.Chem.Soc.Perkin Trans.1991,2:523-526.
102G rner H.; Schulte-Frohlinde D. Upper exeited triplet state mechanism in the trans-cisisomerization of4-bromostilbene [J]. J. Am. Chem. Soc.1979,101,4388-4390.
103Hammond G. S.; Saltie1J.; Lamola A. A. et a1. Mechanisms of photochemical reactions solution.XXII.1photochemical cis-transisomerization [J]. J. Am. Chem. Soc.1964,86,3197-3217.
104Pattabiraman M.; Kaanumalle L. S.; Natarajan A.; Ramamurthy V. Regioselectivephotodimerization of cinnamic acids in water: templation with cucurbiturils [J]. Langmuir.2006,22:7605-7609; Furumi S.; Ichimura K. Surface-assisted photoalignment of discotic liquidcrystals by nonpolarized light irradiation of photo-cross-linkable polymer thin films [J]. J. Phys.Chem. B.2007,111:1277-1287.
105Hecht S.; Khan A. Intramolecular Cross-Linking of Helical Folds:An Approach to OrganicNanotubes [J]. Angew. Chem. Int. Ed.2003,42:6021-6024.
106Zhang J.; Xu J.; Liu S. Chain-Length Dependence of Diblock Copolymer Micellization KineticsStudied by Stopped-Flow pH-Jump [J]. J. Phys. Chem. B.2008,112:11284-11291.
107Ulbrich K.; ubr V. Polymeric anticancer drugs with pH-controlled activation [J]. AdvancedDrug Delivery Reviews.2004,56:1023-1050.
108Cordes E. H.; Bull H. G. Mechanism and Catalysis for Hydrolysis of Acetals, Ketals, and OrthoEsters [J]. Chem Rev.1974,74:581-603.
109Dukkipati A.; Kusnetzow A.; Babu K. R.; Ramos L.; Singh D.; Knox B.E.; Birge R. R.Phototransduction by Vertebrate Ultraviolet Visual Pigments: Protonation of the RetinylideneSchiff Base following Photobleaching [J]. Biochemistry.2002,41:9842-9851.
2Zhao Y. Photocontrollable Block Copolymer Micelles: What Can We Control [J]. J. Mater. Chem.2009,19:4887-4895.
3Shimoboji T.; Larenas E.; Fowler T.; Kulkarni S.; Hoffman A. S.; Stayton P. S. PhotoresponsivePolymer-Enzyme Switches [J]. Proc. Natl. Acad. Sci USA2002,99:16592-16596.
4Ruhmann R. Polymers for Optical Storage-hotoresponsive Polymers by Structure Variation inSide-Group Polymethacrylates [J]. Polym. Int.1997,43:103-108.
5He J.; Tong X.; Zhao Y. Photoresponsive Nanogels Based on Photocontrollable Cross-linkings [J].Macromolecules.2009,42:4845-4852.
6Moniruzzaman M.; Sabey C. J.; Fernando G. F. Photoresponsive Polymers: An Investigation ofTheir Photoinduced Temperature Changes during Photoviscosity Measurements [J]. Polymer.2007,48:255-263.
7Alonso M.; Reboto V.; Guiscardo L.; San M. A.; Rodriguez J. C. Spiropyran Derivative of AnElastin-Like Bioelastic Polymer: Photoresponesive Molecule Machine to Covert Sunlight intoMechanical Work [J]. Macromolecules.2000,33:9480-9482.
8Nagasaki T. Photoresponsive Polymeric Materials for Drug Delivery Systems: Double Targetingwith Photoresponsive Polymers [J]. Drug Delivery Syst.2008,23:637-643.
9Tong X.; Wang G.; Soldera A.; Zhao Y. How Can Azobenzene Block Copolymer Vesicles beDissociated and Reformed by Light?[J]. J. Phys. Chem. B.2005,109:20281-20287.
10Wang G.; Tong X.; Zhao Y. Preparation of Azobenzene-Containing Amphiphilic DiblockCo-polymers for Light-Responsive Micellar Aggregates [J]. Macromolecules2004,37:8911-8917.
11Lin L.; Yan Z.; Gu J.; Zhang Y.; Feng Z.; Yu Y. UV-Responsive Behavior ofAzopyridine-Containing Diblock CopolymericVesicles: Photoinduced Fusion, Disintegration andRearrangement [J]. Macromol. Rapid Commun.2009,30:1089-1093.
12Puntoriero F.; Ceroni P.; Balzani V.; Bergamini G.; V gtle F. Photoswitchable Dendritic Hosts: ADendrimer with Peripheral Azobenzene Groups [J]. J. Am. Chem. Soc.2007,129:10714-10719.
13Yamada M.; Kondo M.; Mamiya J.; Yu Y.; Kinoshita M.; Barrett C. J.; Ikeda T. PhotomobilePolymer Materials: Towards Light-Driven Plastic Motors [J]. Angew. Chem. Int. Ed.2008,47:4986-4988.
14Berkovic G.; Krongauz V.; Weiss V. Spiropyrans and Spirooxazines for Memories and Switches[J]. Chem. Rev.2000,100:1741-1754.
15Sanchez C.; Lebeau B.; Chaput F.; Boilot J. P. Optical Properties of Functional HybridOrganic–Inorganic Nanocomposites [J]. Adv. Mater.2003,15:1969-1994.
16Guo X.; Zhang D.; Zhou Y.; Zhu D. Synthesis and Spectral Investigations of a New Dyad withSpiropyran and Fluorescein Units: Toward Information Processing at the Single Molecular Level[J]. J. Org. Chem.2003,68:5681-5687.
17Mazzi L.D.; Eugenii K.; Itamar W. Amperometric transdusion of optical signals recorded byorganized monolayers of photoisomerizable spiropyran [J]. J.Am.Chem.Soc.1994,116:7413-7414.
18Parthenopoulos D. A.; Rentzepis P. M. Three-dimensional optical storage memory [J]. Science1989,245:843-845.
19Ito Y.; Sugimura N.; Kwon O. H.; Imanishi Y. Enzyme modification by polymers with solubilitiesthat change in response to photoirradiation in organic media [J]. Nat. Biotechnol.1999,17:73-75.
20Kocer A.; Walko M.; Meijberg W.; Ben L. F. A light-activated nanovalve derived from a channelprotein [J]. Science.2005,309:755-758.
21Vlassiouk I.; Park C. D.; Vail S. A.; Gust D.; Smirnov S. Control of Nanopore Wetting by aPhotochromic Spiropyran: A Light-Controlled Valve and Electrical Switch [J]. Nano Lett,2006,6:1013-1017.
22Lee H.; Wu W.; Oh J. K.; Mueller L.; Sherwood G.; Peteanu L.; Kowalewski T.; Matyjasz-ewskiK. Light-Induced Reversible Formation of Polymeric Micelles [J]. Angew. Chem. Int. Ed.2007,46:2453-2457.
23Chen J.; Zeng F.; Wu S.; Zhao J.; Chen Q.; Tong Z. Reversible fluorescence modulation throughenergy transfer with ABC triblock copolymer micelles asscaffoldsw [J]. Chem. Commun.2008,5580-5582.
24Chen J.; Zeng F.; Wu S.; Chen Q.; Tong Z. A Core-Shell Nanoparticle Approach toPhoto-reversible Fluorescence Modulation of a Hydrophobic Dye in AqueousMedia [J]. Chem.Eur. J.2008,14,4851-4860.
25Jin Q.; Liu G.; Ji J. Micelles and Reverse Micelles with a Photo and Themo Double-ResponsiveBlock Copolymer [J]. J. Polym. Sci: Part A: Polym. Chem.2010,48:2855-2861.
26Jiang J.; Tong X.; Morris D.; Zhao Y. Toward Photocontrolled Release Using Light-DissociableBlock Copolymer Micelles [J]. Macromolecules2006,39:4633-4640.
27Vivero-Escoto J.; Slowing I.; Wu C.; and Lin V. S.-Y. Photoinduced Intracellular ControlledRelease Drug Delivery in Human Cells by Gold-Capped Mesoporous Silica Nanosphere [J]. J. Am.Chem. Soc.2009,131:3462-3463.
28Babin J.; Pelletier M.; Lepage M.; Allard J.F.; Morris D.; Zhao Y. A New Two-Photon-SensitiveBlock Copolymer Nanocarrier [J]. Angew. Chem. Int. Ed.2009,48:3329-3332.
29Jiang J.; Tong X.; Zhao Y. A New Design for Light-Breakable Polymer Micelles [J]. J. Am. Chem.Soc.2005,127:8290-8291.
30Jiang X.; Lavender C. A.; Woodcock J. W.; Zhao B. Multiple Micellization and DissociationTransitions of Thermo-and Light-Sensitive Poly(ethylene oxide)-b-poly(ethoxytri(ethylene glycol)acrylate-co-o-nitrobenzyl acrylate) in Water [J]. Macromolecules.2008,41:2632-2643.
31Jiang X.; Jin S.; Zhong Q.; Dadmun M. D.; Zhao B. Stimuli-Induced Multiple Sol-Gel-SolTransitions of Aqueous Solution of a Thermo-and Light-Sensitive Hydrophilic Block Co-polymer[J]. Macromolecules.2009,42:8468-8476.
32Lai J.; Mu X.; Xu Y.; Wu X.; Wu Ch.; Li C.; Chen J.; Zhao Y.; Light-responsive nanogatedensemble based on polymer grafted mesoporous silica hybrid nanoparticles [J]. Chem. Commun.2010,46:7370-7372.
33Ionov L.; Diez S. Environment-Friendly Photolithography UsingPoly(N-isopropylacrylamide)-Based Thermoresponsive Photoresists [J]. J. Am. Chem. Soc.2009,131:13315-13319.
34Ding J.; Liu G. Polystyrene-block-poly(2-cinnamoylethyl methacrylate)Nanospheres withCross-Linked Shells [J]. Macromolecules.1998,31:6554-6558.
35Jiang J.; Qi B.; Lepage M.; Zhao Y. Polymer Micelles Stabilization on Demand throughReversible Photo-Cross-Linking [J]. Macromolecules.2007,40:790-792.
36Sinkel C.; Greiner A.; Agarwal S. Synthesis, Characterization, and Properties Evaluation ofMethylcoumarin End-Functionalized Poly(methyl methacrylate) for Photoinduced Drug Release[J]. Macromolecules.2008,41:3460-3467.
37Iliopoulos K.; Krupka O.; Gindre D.; SalléM. Reversible Two-Photon Optical Data Storage inCoumarin-Based Copolymers [J]. J. Am. Chem. Soc.2010,132,14343-14345.
38Kirmse.W.100Years of the Wolff Rearrangement [J]. Eur. J. Org. Chem.2002,14:2193-2256.
39(a) Almstead, J. I. K.; Urwyler B.; Wirz, J. Flash Photolysis of a-Diazonaphthoquinones inAqueous Solution: Determination of Rates and Equilibria for Keto-Enol Tautomerization of1-Indene-3-carboxylic Acid [J]. J. Am. Chem. Soc.1994,116,954-960.
40Goodwin A. P.; Mynar J. L.; Ma Y.; Fleming G. R.; Fréchet J. M. J. Synthetic Micelle Sensitive toIR Light via a Two-Photon Process [J]. J. Am. Chem. Soc.2005,127:9952-9953.
41Mynar J. L.; Goodwin A. P.; Cohen J. A.; Ma Y.; Fleming G. R.; Fréchet J. M. J. Two-photondegradable supramolecular assemblies of linear-dendritic Copolymers [J]. Chem. Commun.2007,12:2081-2082.
42Horie K.; Mita I. Photoisomerization of Ethyl Cinnamate in Dilute Solutions [J]. J. Photochem.1934,26:185-192.
43Pattanaargson S.; Munhapol T.; Hirunsupachot P.; Luangthongaram P. Photoisomerization of octylmethoxycinnamate [J]. J of Photochem and Photobio A:Chemistry.2004,161:269-274.
44Ishigami T.; Nakazato K.; Uehara M.; Endo T. Marked Dependence of Multiplicity in Direct Z,EPhotoisomerization of a Series of Methyl Cinnamates on Their p-substituents [J]. Tetrahedron Lett.1979,20:863-866.
45Ketner A. M..; Kumar R.; Davies T; S.; Elder P. W.; Raghavan S. R. A Simple Class ofPhotorheological Fluids: Surfactant Solutions with Viscosity Tunable by Light [J]. J. Am. Chem.Soc.2007,129:1553-1559.
46Wijtmans M.; Rosenthal S. J.; Zwanenburg B.; Porter N. A. Visible Light Excitation of CdSeNanocrystals Triggers the Release of Coumarin from Cinnamate Surface Ligands [J]. J. Am. Chem.Soc.2006,128:11720-11726.
47Noyce D. S.; King P. A.; Kirby F. B.; Reed W. L. The Kinetics of the Acid-catalyzedIsomerization of cis-Cinnamic acid [J]. J. Am. Chem. Soc.1962,84:1632-1635.
48Reed G. A.; Dimmel D. R.; and Malcolm E. W. Influence of Nucleophiles on the HighTemperature Aqueous Isomerization of cis-to trans-Cinnamic Acid [J]. J. Org. Chem.1993,58:6364-6371.
49Shindo Y.; Horie K.; Mita I. Rate for Photodimerization of Ethyl Cinnmate in Diluted solution [J].Chem. Lett.1983,18,639-642.
50Shen S.; Torkelson J. M.; Elbed J. E.; Lewis F. D. Thermally irreversible photoresponsivepolymers:Synthesis and preliminary characterization of copolymers containing side-chaintrans-cinnamamide chromophores [J]. Macromol.Chem.phys.1990,191:2367-2375.
51Laschewsky A.; Reka E. D. Photochemical modification of the lower critical solution temperatureof cinnamoylated poly(N-2-hydroxypropylmethacrylamide) in water [J]. Macromol. Rapid.Commun.2000,21:937-940.
52Kawatsuki N.; Yamashita A.; Fujii Y.; Kitamura C.; Yoneda A. Thermally EnhancedPhotoinduced Reorientation in Photo-Cross-Linkable Liquid Crystalline Polymers Comprised ofCinnamate and Tolane Mesogenic Groups [J]. Macromolecules2008,41:9715-9721.
53Liu G.; Hu N.; Xu X.; Yao H. Cross-Linked Polymer Brushes.1. Synthesis of Poly[β-(vinylox y)ethyl cinnamate]-b-poly (isobutyl vinyl ether)[J]. Macromolecules1994,27:3892-3895.
54Guo A.; Liu G.; Tao J. Star Polymers and Nanospheres from Cross-Linkable Diblock Copolymers[J]. Macromolecules.1996,29:2487-2493.
55Tao J.; Stewart S.; Liu G.; Yang M.; Star and Cylindrical Micelles ofPolystyrene-block-poly(2-cinnamoylethyl methacrylate) in Cyclopentane [J]. Macromolecules.1997,30:2738-2745.
56Ding J.; Liu G. Polystyrene-block-poly(2-cinnamoylethyl methacrylate) Nanospheres withCross-Linked Shells [J]. Macromolecules.1998,31:6554-6558.
57Henselwood F.; Liu G. Water-Soluble Nanospheres of Poly(2-cinnamoylethylmethacrylate)-block-poly(acrylic acid)[J].Macromolecules.1997,30:488-493.
58Liu G.; Ding J.; Guo A.; Herfort M.; Bazett-Jones D. Potential Skin Layers for Membranes withTunable Nanochannels [J]. Macromolecules.1997,30,1851-1853.
59Tao J.; Liu G. Polystyrene-block-poly(2-cinnamoylethyl methacrylate) Tadpole Molecules [J].Macromolecules.1997,30:2408-2411.
60Kim J. S.; Jeon H. J.; Park J. J.; Park M. S.; Youk J. H. Encapsulation of Nanomaterials Using anIntermediary Layer Cross-Linkable ABC Triblock Copolymer [J]. J. Polym. Scie: Part A: PolymChem.2009,47:4963-4970.
61John B. M.; Robert H. G. Synthesis of Fluorine-18Functionalized Nanoparticles for use as invivo，Molecular Imaging Agents [J]. J. Am. Chem. Soc.2008,130:6731-6733.
62Jiang X.; Luo S.; Armes S. P.; Shi W.; Liu S. UV Irradiation-Induced Shell Cross-Linked Micelleswith pH-Responsiv e Cores Using ABC Triblock Copolymers [J]. Macromolecules.2006,39:5987-5994.
63Yusa S.; Sugahara M.; Endo T.; Morishima Y. Preparation and Characterization of apH-Responsive Nanogel Based on a Photo-Cross-Linked Micelle Formed From BlockCopolymers with Controlled Structure [J]. Langmuir.2009,25:5258-5265.
64Szczubialka K.; Moczek.; Blaszkiewicz S.; Nowakowska M. Photocrosslinkable SmartTerpolymers Responding to pH Temperature, and Ionic Strength [J]. J. Polym. Scie: Part A:Polym Chem.2004,42:3879-3886.
65Yuan X.; Fischer K.; Sch rtl W. Photocleavable Microcapsules Built from PhotoreactiveNanospheres [J]. Langmuir.2005,21:9374-9380.
66Yuan X.; Fischer K.; Sch rtl W. Reversible Cluster Formation of Colloidal Nanospheres byInterparticle Photodimerization [J]. Adv Funct.Mater.2004,14:457-463.
67Shi D.; Matsusaki M.; Kaneko T.; Akashi M. Photo-Cross-Linking and Cleavage InducedReversible Size Change of Bio-Based Nanoparticles [J]. Macromolecules.2008,41:8167-8172.
68Shi D.; Matsusaki M.; Akashi M. Photo-Cross-Linking Induces Size Change and StealthProperties of Water-Dispersible Cinnamic Acid Derivative Nanoparticles [J]. Bioconjugate Chem.2009,20:1917-1923.
69Chien L-C.; Cada L G. Photo-Cross-Linkable and Optically Active Side-Chain Liquid-CrystallineCopolymers [J]. Macromolecules.1994,27:3721-3726.
70Kawatsuki N.; Matsuyoshi K.; Hayashi M.; Takatsuka H.; Yamamoto T. Photoreaction ofPhoto-cross-linkable Methacrylate Polymer Films Comprising2-CinnamoyloxyethoxybiphenylSide Group by Linearly Polarized Ultraviolet Light and Liquid Crystal Alignment on the ResultantFilms [J]. Chem. Mater.2000,12:1549-1555.
71Furumi S.; Ichimura K. Surface-Assisted Photoalignment of Discotic Liquid Crystals byNonpolarized Light Irradiation of Photo-Cross-Linkable Polymer Thin Films [J]. J. Phys. Chem. B.2007,111:1277-1287.
72Chen W.; Meng F.; Li F.; Ji S.; Zhong Z. pH-Responsive Biodegradable Micelles Based onAcid-Labile,Polycarbonate Hydrophobe: Synthesis and Triggered Drug Release [J].Biomacromolecules.2009,10:1727-1735.
73Gillies E. R.; Fréchet J. M. J. A new approach towards acid sensitive copolymer micelles for drugdelivery [J]. Chem. Commun.2003,12:1640-1641.
74Griset A. P.; Walpole J.; Liu R.; Gaffey A.; Colson Y. L.;Grinstaff M. W. Expansile Nanoparticles:Synthesis, Characterization, and in Vivo Efficacy of an Acid-Responsive Polymeric Drug DeliverySystem [J]. J. Am. Chem. Soc.2009,131:2469-2471.
75Chen D.; Li N.; Gu H.; Xia X.; Xu Q.; Ge J.; Lu J.; Li Y. A novel degradable polymeric carrier forselective release and imaging of magnetic nanoparticles [J]. Chem. Commun.2010,46:6708-6710.
76Gillies E. R.; Jonsson T. B.; Fréchet J. M. J. Stimuli-Responsive Supramolecular Assemblies ofLinear-Dendritic Copolymers [J]. J. Am. Chem.Soc.2004,126:11936-11943.
77Morinaga H.; Morikawa H.; Wang Y.; Sudo A.; Endo T. Amphiphilic Copolymer HavingAcid-Labile Acetal in the Side Chain as a Hydrophobe: Controlled Release of Aldehyde byThermoresponsive Aggregation-Dissociation of Polymer Micelles [J]. Macromolecules.2009,42,2229-2235.
78Shi D.; Matsusaki M.; Akashi M. Photo-tunable protein release from biodegradable nanoparticlescomposed of cinnamic acid derivatives [J]. Journal of Controlled Release.2011,149:182-189.
79Ding J.; Zhuang X.; Xiao C.; Cheng Y.; Zhao L.; He C.; Tang Z.; Chen X. Preparation ofphoto-cross-linked pH-responsive polypeptide nanogels as potential carriers for controlled drugdelivery [J]. J. Mater. Chem.2011,21:11383-11391.
80Schumers J.-M.; Fustin C.-A.; Gohy J.-F. Light-Responsive Block Copolymers [J]. MacromolRapid Commun.2010,31:1588-1607.
81Peris S.; Tylkowski B.; Ronda J. C.; Garcia-Valls R.; Reina J. A.; Giamberini M. Synthesis,Characterization, and Photoresponsive Behavior of New Azobenzene-Containing Polyethers [J]. JPolym Sci, Part A: Polym Chem.2009,47:5426-5436.
82Lin L.; Yan Z.; Gu J.; Zhang Y.; Feng Z.; Yu Y. UV-Responsive Behavior ofAzopyridine-Containing Diblock Copolymeric Vesicles: Photoinduced Fusion, Disintegration andRearrangement [J]. Macromol Rapid Commun.2009,30:1089-1093.
83Yoshida T.; Kanaoka S.; Aoshima S. Living Cationic Polymerization of Azobenzene-ContainingVinyl Ether and Its Photoresponsive Behavior [J]. J. Polym Sci.Part A: Polym Chem.2005,43:5138-5146.
84Yu B.; Jiang X.; Wang R.; Yin J. Multistimuli Responsive Polymer Nanoparticles On the basis ofthe Amphiphilic Azobenzene-Contained Hyperbranched Poly(ether amine)(hPEA-AZO)[J].Macromolecules.2010,43:10457-10465.
85Ling J.; Rong M.; Zhang M. Coumarin imparts repeated photochemical remendability topolyurethan [J]. J. Mater Chem.2011,21:18373-18380.
86Zhao, Y.; Bertrand, J.; Tong, X.; Zhao, Y. Photo-Cross-Linkable Polymer Micelles inHydrogen-Bonding-Built Layer-by-Layer Films [J]. Langmuir.2009,25:13151-13157.
87He J.; Tong X.; Tremblay L.; Zhao, Y. Corona-Cross-Linked Polymer Vesicles Displaying aLarge and Reversible Temperature-Responsive Volume Transition [J]. Macromolecules.2009,42:7267-7270.
88Palczewski K.; Kumasaka T.; Hori T.; Behnke C. A.; Motoshima H.; Fox B. A.; Trong I. L.;Teller,D. C.; Okada T.; Stenkamp R. E.; Yamamoto M.; Miyano M. Crystal structure of rhodopsin: A Gprotein-coupled receptor [J]. Science.2000,289:739-745.
89Li Y.; Tang Y.; Yang K.; Chen X.; Lu L.; Cai Y. Facile Synthesis and Photo-Tunable Properties ofa Photosensitive Polymer Whose Chromophores Bound with pH-Labile Cyclic Acetal Linkages [J].Macromolecules.2008,41:4597-4606.
90Liu Z.; Tang Y.; Li N.; Lu L.; Deng J.; Cai Y. Modulating light-tunable acid sensitivity of abioinspired polymer simply by adjusting the position of a single methoxy substituent [J]. J. Polym.Sci.: Part A: Polym. Chem.2012,50:495-508.
91Lu L.; Zhang H.; Yang N; Cai Y. Toward Rapid and Well-Controlled Ambient TemperatureRAFT Polymerization under UV-Vis Radiation: Effect of Radiation Wave Range [J].Macromolecules.2006,39:3770-3776.
92Sun J.; Peng Y.; Chen Y.; Liu Y.; Deng J.; Lu L.; Cai Y. Effect of Molecular Structure onThermoresponsive Behaviors of Pyrrolidone-Based Water-Soluble Polymers [J]. Macromolecules.2010,43:4041-4049.
93Deng J.; Shi Y.; Jiang W.; Peng Y.; Lu L.; Cai Y. Facile Synthesis and ThermoresponsiveBehaviors of a Well-Defined Pyrrolidone Based Hydrophilic Polymer [J]. Macromolecules.2008,41:3007-3014.
94Boiko N.; Zhu X.; Bobrovsky A.; Shibaev V. First Photosensitive Liquid CrystallineDendrimer:Synthesis, Phase Behavior, and Photochemical Properties [J]. Chem. Mater.2001,13:1447-1452.
95Coqueret X. Photoreactivity of polymers with dimerizable side-groups: Kinetic analysis forprobing morphology and molecular organization [J]. Macromol. Chem. Phys.1999,200:1567-1579.
96Xu F. J.; Li Y. L.; Kang E. T.; Neoh K. G. Heparin-coupled poly(poly(ethyleneglycol)monomethacrylate)-Si(III) hybrids and their blood compatible surfaces [J].Biomacromolecules.2005,6:1759-1768.
97Tao L.; Mantovani G.; Lecolley F.; Haddleton D. M.-Aldehyde terminally functionalmethacrylic polymers from living radical polymerization: application in proteinconjugation"Pegylation"[J]. J. Am. Chem. Soc.2004,126:13220-13221.
98Walter J. M.; Greenfield D.; Bustamante C.; Liphardt J. Light-powering escherichia coli withproteorhodopsin [J]. Proc. Natl. Acad. Sci. U. S. A.2007,104:2408-2412; Schulten K.; Tavan P. A.mechanism for the light-driven proton pump of Halobacterium halobium [J]. Nature1978,272:85-86; Hampp N. Bacteriorhodopsin as a photochromic retinal protein for optical memories [J].Chem. Rev.2000,100:1755-1776.
99Chen R. L.; Liu R. S. H. New hindered isomers of3-dehydroretinal (vitamin A2)[J]. Tetrahedron.1996,52:7809-7816.
100Dugave C.; Demange L. Cis-Trans isomerization of organic molecules andbiomolecules:Implications and Applications [J]. Chem. Rev.2003,103:2475-2532.
101Pfoertner K. H. Novel photosensitizers for the E/Z-isomerization of trienes. Part1.syntheses andapplication [J]. J.Chem.Soc.Perkin Trans.1991,2:523-526.
102G rner H.; Schulte-Frohlinde D. Upper exeited triplet state mechanism in the trans-cisisomerization of4-bromostilbene [J]. J. Am. Chem. Soc.1979,101,4388-4390.
103Hammond G. S.; Saltie1J.; Lamola A. A. et a1. Mechanisms of photochemical reactions solution.XXII.1photochemical cis-transisomerization [J]. J. Am. Chem. Soc.1964,86,3197-3217.
104Pattabiraman M.; Kaanumalle L. S.; Natarajan A.; Ramamurthy V. Regioselectivephotodimerization of cinnamic acids in water: templation with cucurbiturils [J]. Langmuir.2006,22:7605-7609; Furumi S.; Ichimura K. Surface-assisted photoalignment of discotic liquidcrystals by nonpolarized light irradiation of photo-cross-linkable polymer thin films [J]. J. Phys.Chem. B.2007,111:1277-1287.
105Hecht S.; Khan A. Intramolecular Cross-Linking of Helical Folds:An Approach to OrganicNanotubes [J]. Angew. Chem. Int. Ed.2003,42:6021-6024.
106Zhang J.; Xu J.; Liu S. Chain-Length Dependence of Diblock Copolymer Micellization KineticsStudied by Stopped-Flow pH-Jump [J]. J. Phys. Chem. B.2008,112:11284-11291.
107Ulbrich K.; ubr V. Polymeric anticancer drugs with pH-controlled activation [J]. AdvancedDrug Delivery Reviews.2004,56:1023-1050.
108Cordes E. H.; Bull H. G. Mechanism and Catalysis for Hydrolysis of Acetals, Ketals, and OrthoEsters [J]. Chem Rev.1974,74:581-603.
109Dukkipati A.; Kusnetzow A.; Babu K. R.; Ramos L.; Singh D.; Knox B.E.; Birge R. R.Phototransduction by Vertebrate Ultraviolet Visual Pigments: Protonation of the RetinylideneSchiff Base following Photobleaching [J]. Biochemistry.2002,41:9842-9851.
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |