Chiral Borondipyrromethene Dye with Acid-Responsive NIR Emission and Chiral Optical Behavior.

IF 3 4区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

ChemPlusChem Pub Date : 2025-04-08 DOI:10.1002/cplu.202500237

Chunyan Song, Zhenhui Wei, Yongsheng Zhang, Muqian Li, Junbo Gong

引用次数: 0

Abstract

A chiral BODIPY dye, denoted as (R)-2, incorporating near-infrared (NIR) emission and chiral optical behavior was synthesized. The dye was engineered by coupling PEG chains with R-stereogenic centers to a donor-acceptor BODIPY core through a Suzuki coupling reaction. This modification significantly enhances the solubility and facilitates efficient chirality transfer resulting in CD activity, which is quite remakable in organic small molecule solutions. Furthermore, acid-triggered protonation of the dye leads to a bathochromic shift in the maximum absorption wavelength (from 633 to 664 nm) and an increase in NIR emission intensity, which is attributed to the enhanced intramolecular charge transfer in solution.

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具有酸响应性近红外发射和手性光学行为的手性硼二吡咯甲烷染料。

合成了一种具有近红外（NIR）发射特性和手性光学特性的手性BODIPY染料，标记为(R)-2。该染料通过Suzuki偶联反应将具有r-立体中心的PEG链偶联到供体-受体BODIPY核上。这种修饰显著提高了CD的溶解度，促进了有效的手性转移，从而提高了CD的活性，这在有机小分子溶液中是非常明显的。此外，酸触发的质子化导致染料的最大吸收波长（从633 nm到664 nm）发生色移，近红外发射强度增加，这是由于溶液中分子内电荷转移的增强。

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

ChemPlusChem CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

5.90

自引率

0.00%

发文量

200

审稿时长

1 months

期刊介绍： ChemPlusChem is a peer-reviewed, general chemistry journal that brings readers the very best in multidisciplinary research centering on chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. Fully comprehensive in its scope, ChemPlusChem publishes articles covering new results from at least two different aspects (subfields) of chemistry or one of chemistry and one of another scientific discipline (one chemistry topic plus another one, hence the title ChemPlusChem). All suitable submissions undergo balanced peer review by experts in the field to ensure the highest quality, originality, relevance, significance, and validity.