Strategic Acetylation of BODIPY Dyes: Tuning Excited-State Geometry for the Design of Fluorogenic Sensing Probes

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-13 DOI:10.1021/acs.orglett.5c01822

Yeri Kim, Youngmi Kim

引用次数: 0

Abstract

Strategic acetylation and alkylation modulate the photophysical properties of BODIPY dyes. Meso-acetylated D8COMe exhibits a large Stokes shift through excited-state geometric reorganization, while C2-acetylated D2COMe preserves characteristic BODIPY spectral features. Introduction of methyl groups at the C1/C7 positions influences fluorescence efficiency, with T8COMe showing viscosity-dependent emission. Computational analyses confirm structural distortion as the primary mechanism for fluorescence modulation. These structure–property relationships enable the rational design of fluorogenic probes for nucleophilic species detection and viscosity sensing applications.

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BODIPY染料的策略乙酰化：调整荧光传感探针设计的激发态几何

策略乙酰化和烷基化可调节BODIPY染料的光物理性质。中位乙酰化D8COMe通过激发态几何重组表现出较大的Stokes位移，而c2乙酰化D2COMe则保留了BODIPY光谱特征。在C1/C7位置引入甲基会影响荧光效率，T8COMe表现出黏度依赖性发射。计算分析证实结构畸变是荧光调制的主要机制。这些结构-性能关系使荧光探针的亲核物质检测和粘度传感应用的合理设计。

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

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.