π-Extended Ladder-Type Conjugated Polymers via BN-Annulation

Cyclopenta[c]thiophene (CPT)-based polymers are potential candidates in organic electronics. Here, we report the first solution-processable red homopolymer (P1) of a thiophene-capped derivative of CPT (DHTCPT), and a blue homopolymer (P2) of N-substituted thienodiketopyrrolopyrrole (DEHTDPP). Additionally, by alternatingly copolymerizing the DHTCPT and DEHTDPP units, we achieved the green copolymer P3, thus completing the red-green-blue color wheels. We have shown experimentally and computationally (time-dependent density functional theory and natural bond orbital calculations) that P1 and P2 have very different optoelectronic features. However, in a donor–acceptor (D–A) copolymer P3, the optoelectronic properties have been tuned significantly to keep it in an intermediate range of P1 and P2. P2 and P3 absorb throughout the whole UV-vis range of the solar spectrum. Furthermore, all polymers showed electrochromism to switch colors between neutral and polaronic states in solution. For P1, the maximum optical contrast (%ΔT) was observed for the SOMO→LUMO transition, whereas P3 displayed the maximum %ΔT at the HOMO→LUMO transition.

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Recent Advance of 1,2-BN Heteroaromatics in China

Xu¹,

Li²,

Liu³

2023

Chinese Journal of Organic Chemistry

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Polycyclic aromatic hydrocarbons (PAHs) and their derivatives are widely used in the field of organic optoelectronic materials, and the photophyscial properties of polycyclic aromatic hydrocarbons can be effectively modified by heteroatomic doping. By replacing carbon carbon (CC) units with an isoelectronic and isostructural boron nitrogen (BN) units, the electronic structure and intermolecular interactions of PAHs can be fine-tuned, resulting in new BN-heteroaromatics with unique optoelectronic properties and bioactivity. BN/CC isosterism can not only enrich the famlily of heteroaromatics but also promote their applications in the fields of optoelectronic, catalysis and biomedical applications. In particular, the researchers from China have engaged and promoted the development of boron/nitrogen-doped heteroaromaics, leading to some great results. The recent advance of 1,2-BN heteroaromatics in China from the chemistry perspective is summarized, including the synthetic development of 1,2-BN heteroaromatics, as well as their applications in variety of research fields. In the end, the development prospects of BN-heteroaromatics are pointed out. Through highlighting these advances of boron/nitrogen-doped heteroaromaics in China, it is hoped that more researchers will be interested in the synthesis and application of boron/nitrogen-doped heteroaromaics. It is also hoped that this review would stimulate the conversation and cooperation between the chemists and material scientists in the related fields. Keywords boron/nitrogen doped polycyclic aromatic hydrocarbon; isosterism; aromatics; organoboron chemistry 全碳稠环芳烃(PAHs)是由 sp 2 杂化碳原子组成的二维石墨烯片段, 稠环芳烃及其衍生物由于具有独特的光学和电子性能, 在有机光电材料领域备受科学家们的青睐. 近几年, 以稠环芳烃为代表的有机材料在电子器件方面应用广泛, 例如有机发光二极管(OLED)、场效应晶体(OFET)和有机太阳能电池(OSCs) [1] . 相对于无机材料, 有机光电材料的一个优点是可以从分子层面对其结构进行精确改造, 从而获得所需求的性能. 在全碳稠环芳烃的骨架中嵌入杂原子(N、S、Si、O、P 和 B 等)可以有效调节稠环芳烃的电子结构, 进而可以调节其光电物理性质 [2] .1919 年, 朗格缪尔(Langmuir) [3] 以 N 2 O 和 CO 2 之间有机化学综述与进展 1612 http://sioc-journal.cn/

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π-Extended Ladder-Type Conjugated Polymers via BN-Annulation

Cited by 3 publications

References 49 publications

Conjugated ladder polymers: Advances from syntheses to applications

Conjugated ladder polymers: Advances from syntheses to applications

Cyclopenta[c]thiophene- and Diketopyrrolopyrrole-Based Red-Green-Blue Electrochromic Polymers

Recent Advance of 1,2-BN Heteroaromatics in China

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