基于吲哚的阴离子受体的设计合成、结合性质及其自组装
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摘要
本论文利用吲哚单体设计合成了一系列阴离子中性受体,考察了基于吲哚的阴离子受体在溶液中的阴离子结合性质,并应用于一些特定阴离子的选择性识别传感,实现了对氟离子和醋酸根离子的目测识别。同时以阴离子为配位中心,构建了阴离子主导的阴离子配位聚合物。本论文研究工作的主要内容与创新点表现在以下几个方面：
(1)设计合成了一种基于吲哚咔唑和喹喔啉结构的阴离子受体,并应用于阴离子的比色荧光识别。这类基于吲哚的阴离子受体具有平面刚性结构和较大的π芳香体系,因此表现出丰富的光谱特征。受体在乙腈溶液中对醋酸根离子有很强的结合能力和较高的选择性,并在醋酸根离子的作用下发生荧光淬灭。在二甲基亚砜溶剂中,受体对氟离子和醋酸根离子有很好的吸收光谱响应,产生明显的吸收峰红移现象,这些光谱变化伴随着显著的溶液颜色变化,因此这类受体可以用于氟离子和醋酸根离子的目测识别。同时,不同的颜色变化也为我们提供了一种定性区分氟离子和醋酸根离子的方法。受体与醋酸根离子的复合物晶体结构表明,受体的吲哚咔唑结合位点可以和醋酸根离子形成两个相互匹配的氢键作用,从而牢固的地结合在一起。因此,该类受体无论在溶液中还是在固态下都可为Y形状的羧酸根离子提供了一种有效的识别模式。
(2)以上述平面刚性的阴离子受体为结构单元构建了一系列阴离子复合物。这些阴离子包括球形的氟离子和溴离子、Y形的醋酸根离子和苯甲酸根离子、平面三角形的硝酸根离子、正四面体形的硫酸氢根离子和磷酸二氢离子和八面体形的六氟硅酸根离子。深入系统地研究了固态中阴离子的大小、碱性和几何形状对阴离子结合能力、配位模式和组装结构的影响。在阴离子的主导下,通过氢键、π一π堆积和芳香环C-H氢键作用,形成了多种结构各异的阴离子聚集体,如5：6的阴离子复合物、阴离子二聚体和离子链、阳离子通道和三明治状夹心结构。这些结构有助于构建阴离子主导的自组装超分子体系,在阴离子配位化学的研究中具有重要意义。
(3)设计合成了一系列基于吲哚的含有两个结合位点的阴离子受体结构单元,构建了阴离子主导的阴离子配位聚合物。两个相距较远的阴离子结合位点(双吲哚和吲哚咔唑)通过较大的平面刚性分子连接起来,从而大大降低了阴离子结合过程中的静电相互干扰,保证了受体与阴离子结合的氢键强度、拓扑结构和空间维度。结构单元自身可以通过与溶剂分子的氢键作用或者π-π堆积作用,自组装形成一维带状结构或分子二聚体。这类阴离子受体在溶液中按照1：2化学计量比对氟离子、磷酸二氢根离子和醋酸根离子有很强的结合能力,并可作为一种有效的比色传感器用于二甲基亚砜溶液中氟阴离子目测识别。固态结构研究表明,正是由于阴离子受体结构单元独特的空间结构,它们可以与正四面体形状的磷酸二氢阴离子以以一定化学计量比结合,在固态中自组装形成一系列多维网状阴离子配位聚合物。这些多维网状结构中含有独特的磷酸二氢根二聚体和离子链,它们扮演类似于阳离子配位聚合物中金属离子的角色,主导了固态中多维网状结构的自组装超分子体系。但是,没有直接的证据表明溶液中也存在这些超分子聚集体。
In this dissertation a series of well-designed anion receptors based on indole were prepared, their anion binding properties in solution and anion-directed metal-free multidimensional coordination polymer in solid state were investigated. The design, preparation, anion binding properties and anion-directed self-assembly of such anion recetpors were studied in detail, which are summarized as follows:
A new series of indolocarbazole-quinoxalines (DIPZs) were prepared and characterized for effective fluoride and acetate anions sensing. The new indole-based system had a highly flat rigid structure with largeπsystem, and exhibited high binding affinity and sensitivity for acetate and fluoride anions. Receptors gave abundant and unique spectral feature in dimethyl sulfoxide (DMSO). Both fluoride and acetate anions caused a bathochromic shift of the absorption peaks of receptor nitro-substituted DIPZ in DMSO, whereas only fluoride anion resulted in a remarkable shift of the absorption peak of receptor DIPZ in DMSO. Both receptors could also operate as efficient colorimetric sensors for naked-eye detecting of fluoride and acetate anions, and their combined use also offered a simple way for naked-eye distinguishing of these two anions. Notably, the DIPZ system offered novel and excellent receptors for Y-shaped anion both in solution and in crystalline solid through the formation of two hydrogen bonds.
The easy-to-make anion receptor DIPZ was employed as a versatile building block for constructing anion complexes with spherical fluoride and bromide, Y-shaped acetate and benzoate, trigonal nitrate, tetrahedral hydrogen sulfate and dihydrogen phosphate, and octahedral hexafluorosilicate anions. A systematical solid-state study was performed to investigate the influence of the size, basicity and geometry of anionic substrates on anion-binding affinities and modes, even the assembling structures in the solid state. The combination of conventional hydrogen bonding (N-H hydrogen bonding) and other weak interactions (aryl C-H aryl hydrogen bonding andπ-πstacking interaction) led to the formation of a series of anion-assisted supramolecular architectures with specific aggregates, such as 5:6 binding structure, anionic dimer and chain, cationic channel and sandwich-like structure, which have attracted extensive interests in supramolecular chemistry.
Strategies for exploring anionic templates to direct the sophisticated supramolecular assembly have attracted various attentions. Herein, a series of new anion receptors containing two indole-based binding sites bridged by linking spacer pyrazino[2.3-g]quinoxaline were rationally designed and prepared from precursors 2,3-diindol-3'yl quinoxaline and DIPZ. X-ray analysis showed self-connected network and dimeric packing via hydrogen bonding andπ-πstacking interaction in the solid state in the structures. All the three receptors exhibited a series of prominent absorption bands from the expandedπsystem. The novel indole-based expanded receptors were found to strongly and selectively bind F-, AcO- and H2PO4- among the tested anions (F-,Cl-,Br-, AcO-,H2PO4-, HSO4-,NO3-, and ClO4-) and operated as efficient colorimetric sensors for naked-eye detecting of fluoride anion in DMSO solution. These tailored building blocks captured two anions located at far-spaced binding sites, adopting non-interfering anion-binding processes to guarantee the anion-binding affinity, topology and dimensionality. Solid studies elucidated that the neutral receptors interacted with tetrahedral dihydrogen phosphate anion in proper proportions and designed topologies, leading to the formation of a series of multidimensional networks by self-assembly in the solid state. The observation represented the well-characterized phosphate-directed assembly of multidimensional metal-free coordination polymers in the solid state, where the formed phosphate aggregates including dimer encapsulated in indole-mediated hydrogen-bonded pocket and infinite chain behaved as anionic templates to direct the self-assembly. However, no evidences proved such phosphate-directed infinite coordination polymers in solution.
(1)设计合成了一种基于吲哚咔唑和喹喔啉结构的阴离子受体,并应用于阴离子的比色荧光识别。这类基于吲哚的阴离子受体具有平面刚性结构和较大的π芳香体系,因此表现出丰富的光谱特征。受体在乙腈溶液中对醋酸根离子有很强的结合能力和较高的选择性,并在醋酸根离子的作用下发生荧光淬灭。在二甲基亚砜溶剂中,受体对氟离子和醋酸根离子有很好的吸收光谱响应,产生明显的吸收峰红移现象,这些光谱变化伴随着显著的溶液颜色变化,因此这类受体可以用于氟离子和醋酸根离子的目测识别。同时,不同的颜色变化也为我们提供了一种定性区分氟离子和醋酸根离子的方法。受体与醋酸根离子的复合物晶体结构表明,受体的吲哚咔唑结合位点可以和醋酸根离子形成两个相互匹配的氢键作用,从而牢固的地结合在一起。因此,该类受体无论在溶液中还是在固态下都可为Y形状的羧酸根离子提供了一种有效的识别模式。
(2)以上述平面刚性的阴离子受体为结构单元构建了一系列阴离子复合物。这些阴离子包括球形的氟离子和溴离子、Y形的醋酸根离子和苯甲酸根离子、平面三角形的硝酸根离子、正四面体形的硫酸氢根离子和磷酸二氢离子和八面体形的六氟硅酸根离子。深入系统地研究了固态中阴离子的大小、碱性和几何形状对阴离子结合能力、配位模式和组装结构的影响。在阴离子的主导下,通过氢键、π一π堆积和芳香环C-H氢键作用,形成了多种结构各异的阴离子聚集体,如5：6的阴离子复合物、阴离子二聚体和离子链、阳离子通道和三明治状夹心结构。这些结构有助于构建阴离子主导的自组装超分子体系,在阴离子配位化学的研究中具有重要意义。
(3)设计合成了一系列基于吲哚的含有两个结合位点的阴离子受体结构单元,构建了阴离子主导的阴离子配位聚合物。两个相距较远的阴离子结合位点(双吲哚和吲哚咔唑)通过较大的平面刚性分子连接起来,从而大大降低了阴离子结合过程中的静电相互干扰,保证了受体与阴离子结合的氢键强度、拓扑结构和空间维度。结构单元自身可以通过与溶剂分子的氢键作用或者π-π堆积作用,自组装形成一维带状结构或分子二聚体。这类阴离子受体在溶液中按照1：2化学计量比对氟离子、磷酸二氢根离子和醋酸根离子有很强的结合能力,并可作为一种有效的比色传感器用于二甲基亚砜溶液中氟阴离子目测识别。固态结构研究表明,正是由于阴离子受体结构单元独特的空间结构,它们可以与正四面体形状的磷酸二氢阴离子以以一定化学计量比结合,在固态中自组装形成一系列多维网状阴离子配位聚合物。这些多维网状结构中含有独特的磷酸二氢根二聚体和离子链,它们扮演类似于阳离子配位聚合物中金属离子的角色,主导了固态中多维网状结构的自组装超分子体系。但是,没有直接的证据表明溶液中也存在这些超分子聚集体。
In this dissertation a series of well-designed anion receptors based on indole were prepared, their anion binding properties in solution and anion-directed metal-free multidimensional coordination polymer in solid state were investigated. The design, preparation, anion binding properties and anion-directed self-assembly of such anion recetpors were studied in detail, which are summarized as follows:
A new series of indolocarbazole-quinoxalines (DIPZs) were prepared and characterized for effective fluoride and acetate anions sensing. The new indole-based system had a highly flat rigid structure with largeπsystem, and exhibited high binding affinity and sensitivity for acetate and fluoride anions. Receptors gave abundant and unique spectral feature in dimethyl sulfoxide (DMSO). Both fluoride and acetate anions caused a bathochromic shift of the absorption peaks of receptor nitro-substituted DIPZ in DMSO, whereas only fluoride anion resulted in a remarkable shift of the absorption peak of receptor DIPZ in DMSO. Both receptors could also operate as efficient colorimetric sensors for naked-eye detecting of fluoride and acetate anions, and their combined use also offered a simple way for naked-eye distinguishing of these two anions. Notably, the DIPZ system offered novel and excellent receptors for Y-shaped anion both in solution and in crystalline solid through the formation of two hydrogen bonds.
The easy-to-make anion receptor DIPZ was employed as a versatile building block for constructing anion complexes with spherical fluoride and bromide, Y-shaped acetate and benzoate, trigonal nitrate, tetrahedral hydrogen sulfate and dihydrogen phosphate, and octahedral hexafluorosilicate anions. A systematical solid-state study was performed to investigate the influence of the size, basicity and geometry of anionic substrates on anion-binding affinities and modes, even the assembling structures in the solid state. The combination of conventional hydrogen bonding (N-H hydrogen bonding) and other weak interactions (aryl C-H aryl hydrogen bonding andπ-πstacking interaction) led to the formation of a series of anion-assisted supramolecular architectures with specific aggregates, such as 5:6 binding structure, anionic dimer and chain, cationic channel and sandwich-like structure, which have attracted extensive interests in supramolecular chemistry.
Strategies for exploring anionic templates to direct the sophisticated supramolecular assembly have attracted various attentions. Herein, a series of new anion receptors containing two indole-based binding sites bridged by linking spacer pyrazino[2.3-g]quinoxaline were rationally designed and prepared from precursors 2,3-diindol-3'yl quinoxaline and DIPZ. X-ray analysis showed self-connected network and dimeric packing via hydrogen bonding andπ-πstacking interaction in the solid state in the structures. All the three receptors exhibited a series of prominent absorption bands from the expandedπsystem. The novel indole-based expanded receptors were found to strongly and selectively bind F-, AcO- and H2PO4- among the tested anions (F-,Cl-,Br-, AcO-,H2PO4-, HSO4-,NO3-, and ClO4-) and operated as efficient colorimetric sensors for naked-eye detecting of fluoride anion in DMSO solution. These tailored building blocks captured two anions located at far-spaced binding sites, adopting non-interfering anion-binding processes to guarantee the anion-binding affinity, topology and dimensionality. Solid studies elucidated that the neutral receptors interacted with tetrahedral dihydrogen phosphate anion in proper proportions and designed topologies, leading to the formation of a series of multidimensional networks by self-assembly in the solid state. The observation represented the well-characterized phosphate-directed assembly of multidimensional metal-free coordination polymers in the solid state, where the formed phosphate aggregates including dimer encapsulated in indole-mediated hydrogen-bonded pocket and infinite chain behaved as anionic templates to direct the self-assembly. However, no evidences proved such phosphate-directed infinite coordination polymers in solution.
引文
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