One-Pot Synthesis of Vinylogous Cyano Aminoaryls (VinCAs) as Benzenic Fluorophores: Tailoring Diverse Emission Colors for White Light Emitting Materials and Cell Imaging
Saurajit Ghosh, Shubham Kumar, Swathi Suneesh, Himanshi Bhambri, Sanjay K. Mandal, Sarbani Ghosh, Rajdeep Chowdhury and Partha Sarathi Addy*,
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引用次数: 0
Abstract
Donor–acceptor-based organic small molecules with an electronic push–pull effect can demonstrate intramolecular charge transfer to show interesting photoluminescence properties. This is an essential criterion for designing fluorogenic probes for cell imaging studies and the development of organic light-emitting diodes. Now, to design such optical materials sometimes it is necessary to tune the band gap by controlling the energies of the highest occupied molecular orbital and lowest unoccupied molecular orbital. Typically, the band gaps could be modulated by installing unsaturated handles between electron-rich donors and electron-deficient acceptors. However, these methods are often synthetically and economically challenging due to the involvement of expensive catalysts and difficult reaction setups. In our present study, we show a straightforward, cost-effective method for obtaining a series of donor–acceptor-type Vinylogous Cyano Aminoaryls (VinCAs) with diverse emission colors. Further studies reveal that these VinCAs can serve as effective cell imaging agents, showcasing potential use in chemical biology. Additionally, these molecules could be further used to generate white light emission (WLE), showing their potential utility in advanced lighting technologies.
具有电子推拉效应的供体-受体型有机小分子可以通过分子内电荷转移显示出有趣的光致发光特性。这是设计用于细胞成像研究的荧光探针和开发有机发光二极管的基本标准。现在,要设计此类光学材料,有时需要通过控制最高占位分子轨道和最低未占位分子轨道的能量来调整带隙。通常情况下,可以通过在富电子供体和缺电子受体之间安装不饱和手柄来调节带隙。然而,由于涉及昂贵的催化剂和困难的反应设置,这些方法往往在合成和经济上具有挑战性。在本研究中,我们展示了一种简单、经济高效的方法,可以获得一系列具有不同发射颜色的供体-受体型乙烯基氰基氨基芳基(Vinylogous Cyano Aminoaryls,VinCAs)。进一步的研究表明,这些 VinCAs 可作为有效的细胞成像剂,在化学生物学中具有潜在用途。此外,这些分子还可进一步用于产生白光发射(WLE),显示了它们在先进照明技术中的潜在用途。
期刊介绍:
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.