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具有可调光物理和电化学性质的吲哚并[3,2 - b]咔唑基硼配合物的合成

Synthesis of Indolo[3,2- b]carbazole-Based Boron Complexes with Tunable Photophysical and Electrochemical Properties.

作者信息

Mula Soumyaditya, Leclerc Nicolas, Lévêque Patrick, Retailleau Pascal, Ulrich Gilles

机构信息

Institut de Chimie et Procédés pour l'Énergie, l'Environnement et la Santé (ICPEES), UMR CNRS 7515 , Ecole Européenne de Chimie, Polymères et Matériaux (ECPM) , 25 Rue Becquerel , Strasbourg 67087 Cedex 2 , France.

Le Laboratoire des Sciences de l'Ingénieur, de l'Informatique et de l'Imagerie (ICube), UMR7357 , Université de Strasbourg-CNRS , 23 Rue du Loess , Strasbourg 67037 , France.

出版信息

J Org Chem. 2018 Dec 7;83(23):14406-14418. doi: 10.1021/acs.joc.8b01948. Epub 2018 Nov 13.

Abstract

New synthetic strategies were developed for the synthesis of indolo-pyridine boron difluoride (IPBD) dyes and antiladder-type π-conjugated dyes based on the pyridine/pyrazine-indolocarbazole (ICZ) structures. The photophysical and electrochemical properties of the dyes were measured in solution, solid state, and thin films and rationalized by theoretical calculations. Interestingly, these properties of the dyes can be tuned in a wide range using the developed chemical route. For example, the absorption range and fluorescence color of the dyes in solution and solid state and the HOMO-LUMO energy gaps were tuned by structure modulations. The absorption properties of those new boron complexes cover most of the UV-visible-NIR spectrum. Therefore, this appealing tunability feature makes these new types of dyes very promising candidates for their further use in functional material development.

摘要

开发了新的合成策略,用于合成基于吡啶/吡嗪-吲哚并咔唑(ICZ)结构的吲哚-吡啶二氟化硼(IPBD)染料和反梯形π共轭染料。在溶液、固态和薄膜中测量了这些染料的光物理和电化学性质,并通过理论计算进行了合理化分析。有趣的是,使用所开发的化学路线可以在很宽的范围内调节这些染料的性质。例如,通过结构调制来调节染料在溶液和固态中的吸收范围、荧光颜色以及HOMO-LUMO能隙。那些新型硼配合物的吸收特性覆盖了大部分紫外-可见-近红外光谱。因此,这种吸引人的可调谐特性使这些新型染料成为功能材料开发中进一步应用的非常有前景的候选者。

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