Optimized and Scalable Synthesis of BOPYRENPY Chromophores: Access to a Seven-Membered BF2-C60 Dyad for Reactive Oxygen Species Generation.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-01 DOI:10.1021/acs.orglett.5c03720

Edwin J Gonzalez Lopez,Claudia Chávez Hernández,Sofia Santamarina,Daniel A Heredia

引用次数: 0

Abstract

We report an optimized and scalable synthesis of BOPYRENPY, a seven-membered BF2-chelated chromophore, improving yields from 10% to almost 90%, on a multigram scale via acetonitrile-mediated stabilization of BF3 intermediates. This approach enabled the first covalently linked seven-membered BF2-C60 dyad, previously inaccessible due to low precursor availability. Optical and electrochemical studies demonstrate efficient intramolecular energy and electron transfer to the fullerene triplet state, driving the generation of reactive oxygen species (ROS) and establishing a new heavy-atom-free triplet photosensitizer platform for ROS-mediated applications.

查看原文本刊更多论文

BOPYRENPY发色团的优化和可扩展合成：用于活性氧生成的七元BF2-C60二偶体的获取

我们报道了一种优化和可扩展的合成BOPYRENPY，一种七元bf2螯合发色团，通过乙腈介导的BF3中间体稳定，在多图尺度上将产率从10%提高到近90%。这种方法实现了第一个共价连接的七元BF2-C60二偶体，以前由于前体可用性低而无法获得。光学和电化学研究证明了分子内能量和电子向富勒烯三重态的有效转移，推动了活性氧（ROS）的产生，并为ROS介导的应用建立了一个新的无重原子三重态光敏剂平台。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

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.