Tunable full-color dual-state (solution and solid) emission of push-pull molecules containing the 1-pyrindane moiety.

IF 2.2 4区 化学 Q2 CHEMISTRY, ORGANIC
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-19 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.251
Anastasia I Ershova, Sergey V Fedoseev, Konstantin V Lipin, Mikhail Yu Ievlev, Oleg E Nasakin, Oleg V Ershov
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引用次数: 0

Abstract

A facile method for the synthesis of arylidene derivatives of pyrindane - (E)-7-arylmethylene-2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine-3,4-dicarbonitriles - was developed. Tunable full-color emission was achieved for the synthesized push-pull molecules, solely by changing donor groups while keeping both the conjugated system and acceptor part of the molecule unchanged. This represents a rare approach for the design of such fluorophores. Arylidene derivatives of pyrindane were found to be efficient fluorescent dyes showing a moderate to high emission quantum yield. The push-pull molecules were also characterized by a dual-state emission (in solution and in the solid state). Emission maxima ranged from 469 to 721 nm in solution depending on the solvent and type of donor substituent, and from 493 to 767 nm in the solid state. For the arylidene derivative of pyrindane with a dimethylamino group, it was shown that fluorescence can be changed by the action of an acid both in solution and in the solid state.

含有 1-pyrindane 分子的推拉式分子的可调谐全彩双态(溶液和固体)发射。
本研究开发了一种简便的方法来合成吡啶烷芳基衍生物--(E)-7-芳基亚甲基-2-氯-6,7-二氢-5H-环戊并[b]吡啶-3,4-二甲腈。在保持共轭体系和分子受体部分不变的情况下,通过改变供体基团,合成的推拉式分子实现了可调的全彩发射。这是设计此类荧光团的一种罕见方法。研究发现,吡啶烷芳基衍生物是一种高效的荧光染料,具有中等到较高的发射量子产率。推拉式分子还具有双态发射(溶液和固态)的特点。根据溶剂和供体取代基类型的不同,溶液中的最大发射波长为 469 至 721 纳米,固态中的最大发射波长为 493 至 767 纳米。对于带有二甲基氨基基团的吡啶烷芳基衍生物,研究表明其在溶液和固态中的荧光都能在酸的作用下发生变化。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
CiteScore
4.90
自引率
3.70%
发文量
167
审稿时长
1.4 months
期刊介绍: The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.
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