Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene.

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2025-02-04 eCollection Date: 2025-01-01 DOI:10.3762/bjoc.21.19

Islam S Marae, Jingyun Tan, Rengo Yoshioka, Zakaria Ziadi, Eugene Khaskin, Serhii Vasylevskyi, Ryota Kabe, Xiushang Xu, Akimitsu Narita

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Abstract

A benzo[rst]pentaphene (BPP) substituted by an isopropoxy group (BPP-OiPr) was synthesized in a facile manner. Its photophysical properties were investigated by UV-vis absorption and fluorescence spectroscopy in compassion to pristine BPP and its oxidation product, benzo[rst]pentaphene-5,8-dione (BPP-dione). BPP-OiPr exhibited a significantly enhanced photoluminescence quantum yield (PLQY), reaching 73% in comparison to pristine BPP (13%). BPP-dione, when compared to the parent BPP, also displayed improved absorption and emission from the first excited singlet (S₁) state with a PLQY of 62% and an intramolecular charge-transfer character. The rod-like nano- to microcrystals as well as longer wires of these BPPs were also revealed by scanning electron microscopy. The intriguing optical properties of BPP and its derivatives may lead to their application as fluorophores.

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.