联二酰肼衍生物和联1，3，4-噁二唑衍生物的合成、自组装与性质研究
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摘要
基于分子间弱相互作用构建超分子自组装体系在生命科学和材料科学领域具有非常重要的意义。本论文在前期研究的基础上，设计并合成了四个系列化合物，即双楔形和线形联二酰肼衍生物N’，N’-二[3，4，5-三(烷氧基链)苯甲酰基]草酰肼 FH-Tn(n=3，4，5，6，7，8，10)、N，N’-二[4-对烷氧基苯甲酰基]草酰肼FH-n(n=3，4，5，6，7，8，10，16)和N，N’-二[4-异辛氧基苯甲酰基]草酰肼FH-Z8，线形联和双楔形1，3，4-噁二唑衍生物2，2-二(对烷氧基苯基)-联(1，3，4-噁二唑)BOXD-n(n=1，3，4，5，6，7，8，10，16)和2，2-二(3，4，5-三(烷氧基链)苯基)-联(1，3，4-噁二唑)BOXD-Tn(n=3，4，5，6，7，8，10，14)。系统研究了两类体系在溶液中和本体状态下的组装行为，探讨了分子结构因素(分子的几何形状、分子尾端烷基链长度、分子间相互作用等)对体系的液晶行为、有机凝胶行为的影响，从分子层面揭示了分子有序聚集的驱动力。获得了基于分子间四重氢键的超分子体系和具有较强荧光量子效率的基于联1，3，4-噁二唑衍生物的超分子体系。论文的主要结果如下：
1．在低浓度的氯仿溶液中(<255μM)，双楔形联二酰肼衍生物FH-T7以单分散状态存在，酰胺基团形成分子内氢键，随浓度增加，发生六元环分子内氢键向五元环分子内氢键的构象转变。高浓度氯仿溶液和本体状态下，FH-Tn分子基于分子间四重氢键形成超分子链。测得FH-T7基于NH-1和NH-2的键合常数分别为447．5和217．2 M～1。与之相对，具有支化烷基链的线形联二酰肼衍生物FH-Z8在高浓度氯仿溶液中，形成基于联二酰肼基团的分子间四重氢键作用和π-π 作用协同的超分子聚集体。FH-Z8基于NH-1和NH-2的键合常数分别为2．2×10～3M～1和1．8×10～3 M～1。
2．FH-Tn(n=6，7，8，10)呈双向柱状液晶相，在液晶态，分子间形成分子间氢键并进一步堆砌成柱状液晶态。FH-Tn在乙醇中可以形成有机凝胶。其凝胶能力、形貌、分子排列模式和分子间氢键强度等受尾端烷基链的影响很大，FH-T6和FH-T7在乙醇中表现出非常强的凝胶能力，临界浓度分别为2．1×10～-3mol L～-1和2．3×10～-3 mol L～-1。在FH-Tn(n=5，6，7)的凝胶中观察到了具有非均一螺距的左旋和右旋纳米带。FH-Z8具有凝胶1，2二氯乙烷的能力，其形成凝胶的临界浓度为0．14 wt％。以上研究结果表明：联二酰肼基团是形成超分子聚集体的有效的开放型分子间四重氢键构筑基元。
3．对BOXD-3和BOXD-T3的分子模拟和BOXD-1的单晶结构分析表明：该类联1，3，4-噁二唑衍生物具有全共轭结构。STM研究表明BOXD-7和BOXD-16在HOPG上形成完美的2D结构，面对面的和肩对肩的电子给体-受体作用是其形成超分子有序结构的主要驱动力。线形BOXD-n呈现丰富的液晶相如向列相、具有较大相变焓和大角度倾斜的近晶C相(倾斜角约50°)和高有序近晶相。在基片没有经过任何取向的情况下，在BOXD-5的Sm X相中观测到大面积单畴区域。双楔形BOXD-Tn分子随尾端烷基链的长度的不同，呈现六方柱状和长方柱状液晶相。BOXD-T14呈现高有序室温六方柱状相。结合单晶分析结果和STM研究结果，确认分子间基于1，3，4-噁二唑环与苯环间的电荷给体-受体作用是该系列化合物呈现具有较大相变焓和大角度倾斜的近晶C相的微观成因。
4．BOXD-n和BOXD-Tn在非极性溶剂和固体下都表现出非常强的荧光发射(在环己烷中Φ_F>90％，BOXD-6固体粉末Φ_F=57％)。BOXD-Tn在溶液中的荧光发射峰表现出溶液极性依赖性(溶液极性增加，荧光发射峰红移，并伴随荧光量子效率的降低)。BOXD-Tn在稀溶液中(1×10～-3 mol/L)为单分散状态并表现分子内电荷转移的特征。BOXD-Tn在不同溶剂体系中可以形成纳米粒子、纤维、螺旋等多种形貌的聚集。通过在BOXD-Tn的DMSO溶液中加入水的办法获得了高荧光量子效率的BOXD-Tn纳米粒子(Φ_F≈60％)。BOXD-T4和BOxD-T5可在DMSO中形成具有高荧光发射的凝胶，其干凝胶的荧光量子效率分别可达100％和72％。这是目前报道的在固体下表现出的最高的荧光量子效率。BOXD-T8在DMSO中可以自组装形成具有蓝色荧光发射的纳米粒子并逐渐发展为纳米螺旋纤维(据我们所知，这是第一例观察到非手性π共轭分子自组装形成纳米粒子，并由纳米粒子发展形成螺旋纤维)；BOXD-T8在乙醇中可以自组装形成纳米纤维，并进一步形成具有荧光增强性的有机凝胶。
Self-assembly of molecules through noncovalent interactions into various superstructures opens new possibilities of constructing novel materials in biology and materials fields. We have designed and synthesized four series twin-tapered and linear-shaped bi-dihydrazide derivatives Oxalyl acid N’, N’-di(3, 4, 5-trialkoxybenzoyl)-hydrazide FH-Tn (n = 3, 4, 5, 6, 7, 8, 10), Oxalyl acid N’, N’-di(4-alkoxybenzoyl)-hydrazide FH-n (n = 3, 4, 5, 6, 7, 8, 10, 16), Oxalyl acid N’, N’-di(4-(2-ethylhexyloxy)benzoyl)-hydrazide FH-Z8 and linear-shaped and twin-tapered bi-1,3,4-oxadiazole derivatives 2, 2-Bis(4-alkoxyphenyl)-bi-1, 3, 4-oxadiazole BOXD-n (n = 1, 3, 4, 5, 6, 7, 10, 16) and 2, 2-Bis(3, 4, 5-trialkoxyphenyl)-bi-1, 3, 4-oxadiazole BOXD-Tn (n = 3, 4, 5, 6, 7, 8, 10, 14). The self-assembly behaviors of the FH-Tn, FH-Z8 and BOXD-Tn and BOXD-n either in solutions or in bulk were systematically investigated, and the effect of molecular structures (molecular geometry, length of the terminal chains and intermolecular interactions, etc.) on their liquid crystalline behaviors and gellation behaviors was discussed to understand the driving force for their self-assembly on molecular level. It was confirmed that bi-dihydrazide unit block can be used to construct supramolecules through self-complementary quadruple hydrogen-bonding. Electron DA interaction was demonstrated to be the driving force for the self assembly of bi-1,3,4-oxadiazole derivatives, which exhibited high. The obtained results were outlined as follows:
Twin-tapered bi-dihydrazide derivatives FH-Tn were involved in intramolecular hydrogen bonding between amide groups in monomer, and there existed conformational transitions, e.g. from 6-membered rings to 5-membered rings intramolecular H-bonding upon concentrating at lower concentrations (< 255 M). Results from 1H NMR diluting experiments, FTIR spectroscopy and mass spectroscopy revealed that intermolecular H-bonds are the main driving force for the formation of supramolecular chains of FH-Tn either in chloroform at higher concentrations or in bulk. Enantiotropic columnar phases were observed in FH-Tn (n = 6, 7, 8, 10) and room temperature column hexagonal phases were obtained by air-drying the chloroform solutions of FH-T6, and FH-T7. In addition, FH-Tn (n = 3, 4, 5, 6, 7, 8, 10) are effective gelators in ethanol. The gelling ability in ethanol, the morphologies, packing structures and intermolecular H-bonding strength were significantly influenced by the length of the alkoxy chains. FH-T6 and FH-T7 showed strong gelation ability in ethanol with critical gelation concentrations of 2.1×10-3 mol L-1 and 2.3×10-3 mol L-1 respectively. Both left- and right-handed helical ribbons with non-uniform helical pitch were observed in FH-Tn (n = 5, 6, 7) gels. Linear shaped bi-dihydrazide derivative FH-Z8 with branched terminal alkyl chains self-assemblies to supramolecules through quadruple hydrogen bonds between bi-dihydrazide units and - interactions in chloroform at higher concentrations. The association constants (K) in chloroform were 2.2×103 M-1 and 1.8×103 M-1 based on NH1 and NH2 in FH-Z8, respectively, which are relatively larger than that of the twin-tapered FH-T7. FH-Z8 could gel dichloroethane with the critical gelation concentrations (CGC) of 0.14 wt%, and spontaneously crystallization from its gel upon storage at room temperature. These results suggested that bi-dihydrazide units could be used as self-complementary quadruple hydrogen-bonding units to assemble new supramolecules.
Fully conjugated conformations were demonstrated either by computer simulation of BOXD-n and BOXD-Tn or in single-crystal state of BOXD-1. Well-defined 3D DA architectures with strong face-to-face and edge-to-edge donor-acceptor interactions were observed in the sing-crystal structure of BOXD-1. Nematic phase, SmC phase with large tilted angle ( 50°) and relatively large transition enthalpic values and a highly ordered SmX phase were demonstrated in BOXD-n (n = 5, 6, 7, 8, 10, 16) through tailing the terminal chains and relatively large scale monodomains were prepared in the SmX phase of BOXD-5 even without any surface treatment. Strong blue fluorescent emissions were observed in BOXD-6 either in cyclohexane ( F 92 %) or in solid state ( F 57 %). The strong donor-acceptor interaction between alkyoxyphenylene ring and 1,3,4-oxadiazole ring was thought to be the driving force for the molecules to self-assemble into large angle tilted layered structure. The columnar mesophases for BOXD-Tn (n = 5, 6, 7, 8, 10) were observed even at low temperature (-20 ) during cooling. A room temperature Colho phase was obtained for BOXD-T14. All the compounds have been demonstrated to exhibit good fluorescence properties either in cyclohexane solution or in bulk. BOXD-Tn showed monomeric feature and intramolecular charge transition at concentrations lower than 1×10-5 mol/L. Extremely strong luminescent gels and nanoparticles based on BOXD-Tn were prepared by tailing the length of the terminal chains. The xerogel of BOXD-T4 shows very strong fluorescence in the blue spectral region ( max = 423 nm) with an efficiency F up to 100 %. To the best of our knowledge, this is the strongest fluorescence quantum yield reported in solid states.BOXD-T8 molecules self-assembled to nanoparticles and further to helical nanofibers with blue fluorescence emission in DMSO, while nanoribbons which resulted in emission-enhanced gel of ethanol. The strong fluorescent emissions of BOXD-T8 in isolated state in apolar solvents were attributed to coplanar conformation of the rigid backbone and the strong fluorescent emissions of BOXD-T8 in the aggregation states were attributed to the coplanar conformation of the rigid backbone and J-aggregation. To the best of our knowledge, this is the first observation of evolution of nanoparticles to helical fibers of an achiral linear -conjugated molecule.
1．在低浓度的氯仿溶液中(<255μM)，双楔形联二酰肼衍生物FH-T7以单分散状态存在，酰胺基团形成分子内氢键，随浓度增加，发生六元环分子内氢键向五元环分子内氢键的构象转变。高浓度氯仿溶液和本体状态下，FH-Tn分子基于分子间四重氢键形成超分子链。测得FH-T7基于NH-1和NH-2的键合常数分别为447．5和217．2 M～1。与之相对，具有支化烷基链的线形联二酰肼衍生物FH-Z8在高浓度氯仿溶液中，形成基于联二酰肼基团的分子间四重氢键作用和π-π 作用协同的超分子聚集体。FH-Z8基于NH-1和NH-2的键合常数分别为2．2×10～3M～1和1．8×10～3 M～1。
2．FH-Tn(n=6，7，8，10)呈双向柱状液晶相，在液晶态，分子间形成分子间氢键并进一步堆砌成柱状液晶态。FH-Tn在乙醇中可以形成有机凝胶。其凝胶能力、形貌、分子排列模式和分子间氢键强度等受尾端烷基链的影响很大，FH-T6和FH-T7在乙醇中表现出非常强的凝胶能力，临界浓度分别为2．1×10～-3mol L～-1和2．3×10～-3 mol L～-1。在FH-Tn(n=5，6，7)的凝胶中观察到了具有非均一螺距的左旋和右旋纳米带。FH-Z8具有凝胶1，2二氯乙烷的能力，其形成凝胶的临界浓度为0．14 wt％。以上研究结果表明：联二酰肼基团是形成超分子聚集体的有效的开放型分子间四重氢键构筑基元。
3．对BOXD-3和BOXD-T3的分子模拟和BOXD-1的单晶结构分析表明：该类联1，3，4-噁二唑衍生物具有全共轭结构。STM研究表明BOXD-7和BOXD-16在HOPG上形成完美的2D结构，面对面的和肩对肩的电子给体-受体作用是其形成超分子有序结构的主要驱动力。线形BOXD-n呈现丰富的液晶相如向列相、具有较大相变焓和大角度倾斜的近晶C相(倾斜角约50°)和高有序近晶相。在基片没有经过任何取向的情况下，在BOXD-5的Sm X相中观测到大面积单畴区域。双楔形BOXD-Tn分子随尾端烷基链的长度的不同，呈现六方柱状和长方柱状液晶相。BOXD-T14呈现高有序室温六方柱状相。结合单晶分析结果和STM研究结果，确认分子间基于1，3，4-噁二唑环与苯环间的电荷给体-受体作用是该系列化合物呈现具有较大相变焓和大角度倾斜的近晶C相的微观成因。
4．BOXD-n和BOXD-Tn在非极性溶剂和固体下都表现出非常强的荧光发射(在环己烷中Φ_F>90％，BOXD-6固体粉末Φ_F=57％)。BOXD-Tn在溶液中的荧光发射峰表现出溶液极性依赖性(溶液极性增加，荧光发射峰红移，并伴随荧光量子效率的降低)。BOXD-Tn在稀溶液中(1×10～-3 mol/L)为单分散状态并表现分子内电荷转移的特征。BOXD-Tn在不同溶剂体系中可以形成纳米粒子、纤维、螺旋等多种形貌的聚集。通过在BOXD-Tn的DMSO溶液中加入水的办法获得了高荧光量子效率的BOXD-Tn纳米粒子(Φ_F≈60％)。BOXD-T4和BOxD-T5可在DMSO中形成具有高荧光发射的凝胶，其干凝胶的荧光量子效率分别可达100％和72％。这是目前报道的在固体下表现出的最高的荧光量子效率。BOXD-T8在DMSO中可以自组装形成具有蓝色荧光发射的纳米粒子并逐渐发展为纳米螺旋纤维(据我们所知，这是第一例观察到非手性π共轭分子自组装形成纳米粒子，并由纳米粒子发展形成螺旋纤维)；BOXD-T8在乙醇中可以自组装形成纳米纤维，并进一步形成具有荧光增强性的有机凝胶。
Self-assembly of molecules through noncovalent interactions into various superstructures opens new possibilities of constructing novel materials in biology and materials fields. We have designed and synthesized four series twin-tapered and linear-shaped bi-dihydrazide derivatives Oxalyl acid N’, N’-di(3, 4, 5-trialkoxybenzoyl)-hydrazide FH-Tn (n = 3, 4, 5, 6, 7, 8, 10), Oxalyl acid N’, N’-di(4-alkoxybenzoyl)-hydrazide FH-n (n = 3, 4, 5, 6, 7, 8, 10, 16), Oxalyl acid N’, N’-di(4-(2-ethylhexyloxy)benzoyl)-hydrazide FH-Z8 and linear-shaped and twin-tapered bi-1,3,4-oxadiazole derivatives 2, 2-Bis(4-alkoxyphenyl)-bi-1, 3, 4-oxadiazole BOXD-n (n = 1, 3, 4, 5, 6, 7, 10, 16) and 2, 2-Bis(3, 4, 5-trialkoxyphenyl)-bi-1, 3, 4-oxadiazole BOXD-Tn (n = 3, 4, 5, 6, 7, 8, 10, 14). The self-assembly behaviors of the FH-Tn, FH-Z8 and BOXD-Tn and BOXD-n either in solutions or in bulk were systematically investigated, and the effect of molecular structures (molecular geometry, length of the terminal chains and intermolecular interactions, etc.) on their liquid crystalline behaviors and gellation behaviors was discussed to understand the driving force for their self-assembly on molecular level. It was confirmed that bi-dihydrazide unit block can be used to construct supramolecules through self-complementary quadruple hydrogen-bonding. Electron DA interaction was demonstrated to be the driving force for the self assembly of bi-1,3,4-oxadiazole derivatives, which exhibited high. The obtained results were outlined as follows:
Twin-tapered bi-dihydrazide derivatives FH-Tn were involved in intramolecular hydrogen bonding between amide groups in monomer, and there existed conformational transitions, e.g. from 6-membered rings to 5-membered rings intramolecular H-bonding upon concentrating at lower concentrations (< 255 M). Results from 1H NMR diluting experiments, FTIR spectroscopy and mass spectroscopy revealed that intermolecular H-bonds are the main driving force for the formation of supramolecular chains of FH-Tn either in chloroform at higher concentrations or in bulk. Enantiotropic columnar phases were observed in FH-Tn (n = 6, 7, 8, 10) and room temperature column hexagonal phases were obtained by air-drying the chloroform solutions of FH-T6, and FH-T7. In addition, FH-Tn (n = 3, 4, 5, 6, 7, 8, 10) are effective gelators in ethanol. The gelling ability in ethanol, the morphologies, packing structures and intermolecular H-bonding strength were significantly influenced by the length of the alkoxy chains. FH-T6 and FH-T7 showed strong gelation ability in ethanol with critical gelation concentrations of 2.1×10-3 mol L-1 and 2.3×10-3 mol L-1 respectively. Both left- and right-handed helical ribbons with non-uniform helical pitch were observed in FH-Tn (n = 5, 6, 7) gels. Linear shaped bi-dihydrazide derivative FH-Z8 with branched terminal alkyl chains self-assemblies to supramolecules through quadruple hydrogen bonds between bi-dihydrazide units and - interactions in chloroform at higher concentrations. The association constants (K) in chloroform were 2.2×103 M-1 and 1.8×103 M-1 based on NH1 and NH2 in FH-Z8, respectively, which are relatively larger than that of the twin-tapered FH-T7. FH-Z8 could gel dichloroethane with the critical gelation concentrations (CGC) of 0.14 wt%, and spontaneously crystallization from its gel upon storage at room temperature. These results suggested that bi-dihydrazide units could be used as self-complementary quadruple hydrogen-bonding units to assemble new supramolecules.
Fully conjugated conformations were demonstrated either by computer simulation of BOXD-n and BOXD-Tn or in single-crystal state of BOXD-1. Well-defined 3D DA architectures with strong face-to-face and edge-to-edge donor-acceptor interactions were observed in the sing-crystal structure of BOXD-1. Nematic phase, SmC phase with large tilted angle ( 50°) and relatively large transition enthalpic values and a highly ordered SmX phase were demonstrated in BOXD-n (n = 5, 6, 7, 8, 10, 16) through tailing the terminal chains and relatively large scale monodomains were prepared in the SmX phase of BOXD-5 even without any surface treatment. Strong blue fluorescent emissions were observed in BOXD-6 either in cyclohexane ( F 92 %) or in solid state ( F 57 %). The strong donor-acceptor interaction between alkyoxyphenylene ring and 1,3,4-oxadiazole ring was thought to be the driving force for the molecules to self-assemble into large angle tilted layered structure. The columnar mesophases for BOXD-Tn (n = 5, 6, 7, 8, 10) were observed even at low temperature (-20 ) during cooling. A room temperature Colho phase was obtained for BOXD-T14. All the compounds have been demonstrated to exhibit good fluorescence properties either in cyclohexane solution or in bulk. BOXD-Tn showed monomeric feature and intramolecular charge transition at concentrations lower than 1×10-5 mol/L. Extremely strong luminescent gels and nanoparticles based on BOXD-Tn were prepared by tailing the length of the terminal chains. The xerogel of BOXD-T4 shows very strong fluorescence in the blue spectral region ( max = 423 nm) with an efficiency F up to 100 %. To the best of our knowledge, this is the strongest fluorescence quantum yield reported in solid states.BOXD-T8 molecules self-assembled to nanoparticles and further to helical nanofibers with blue fluorescence emission in DMSO, while nanoribbons which resulted in emission-enhanced gel of ethanol. The strong fluorescent emissions of BOXD-T8 in isolated state in apolar solvents were attributed to coplanar conformation of the rigid backbone and the strong fluorescent emissions of BOXD-T8 in the aggregation states were attributed to the coplanar conformation of the rigid backbone and J-aggregation. To the best of our knowledge, this is the first observation of evolution of nanoparticles to helical fibers of an achiral linear -conjugated molecule.
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