Synthesis of BIII Suboxochlorins

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-02-28 DOI:10.1021/acs.orglett.5c00304

Xiaorong Jin, Boyu Xiao, Yutao Rao, Mingbo Zhou, Bangshao Yin, Ling Xu, Tomohiro Higashino, Atsuhiro Osuka, Jianxin Song

引用次数: 0

Abstract

As a new core-modified variant of B^III subporphyrins, B^III suboxochlorins were synthesized from B^III meso-2-formylphenylsubporphyrins via addition reaction with mesitylmagnesium bromide, Friedel–Crafts type cyclization effected with BF₃·OEt₂, and oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or AgPF₆. The synthesized B^III suboxochlorins are equipped with a fused and conjugated benzocyclohexene unit at the periphery and display broad and blue-shifted Soret bands and red-shifted and vibronic structured Q-bands as compared with the usual B^III triarylsubporphyrins. These B^III suboxochlorins emit fluorescence, showing a peak over 700 nm and a tail reaching 1000 nm with ca. 2.8% quantum yield.

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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.

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