Discrete boronate ester ladders from the dynamic covalent self-assembly of oligo(phenylene ethynylene) derivatives and phenylenebis(boronic acid),Organic Chemistry Frontiers

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Discrete boronate ester ladders from the dynamic covalent self-assembly of oligo(phenylene ethynylene) derivatives and phenylenebis(boronic acid)
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-03-06 , DOI: 10.1039/d0qo00083c
Vasileios Drogkaris _{1,

2,

3,

4} , Brian H. Northrop _{1,

2,

3,

4}

Affiliation

Three increasingly π-conjugated covalent organic polygons have been prepared by the dynamic covalent condensation of catechol-based oligo(phenylene ethynylene) derivatives with phenylenebis(boronic acid). The assemblies represent a series of boronate ester “ladders” wherein two electron rich oligo(phenylene ethynylene) “rungs” are bridged by electron deficient aryl boronate ester “rails”, resulting in quasi-two-dimensional oligomers of increasing size. Spectroscopic and computational investigations suggest that the ladders exhibit a greater effective conjugation length than comparable oligo(phenylene ethynylene) compounds not bridged by aryl boronate esters. Different conformations, substitutions, and constitutions of boronate ester ladders are also modeled to gain further insight into their influence on π-conjugation and HOMO–LUMO gaps of isolated one-dimensional versus bridged, quasi-two-dimensional conjugated organic materials.

中文翻译：

低聚（亚苯基亚乙炔基）衍生物和亚苯基双（硼酸）的动态共价自组装的离散硼酸酯阶梯

通过基于邻苯二酚的低聚（亚苯基乙炔基）衍生物与亚苯基双（硼酸）的动态共价缩合，制备了三种越来越多的共轭π共价有机多边形。组件代表一系列硼酸酯“梯形”，其中两个富电子的低聚（亚苯基乙炔基）“梯级”通过缺电子的芳族硼酸酯“轨”桥接，导致尺寸增大的准二维低聚物。光谱和计算研究表明，与未由芳基硼酸酯桥接的类似低聚（亚苯基乙炔基）化合物相比，梯子的有效共轭长度更大。不同的构型，替换，与桥接的准二维共轭有机材料

更新日期：2020-03-06

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