Efficient synthesis of conjugated 2-(9H-fluoren-7-yl)-9H-fluorene via Br elimination in 2-bromofluorene using electron beam-irradiation

IF 2.8 3区物理与天体物理 Q3 CHEMISTRY, PHYSICAL

Radiation Physics and Chemistry Pub Date : 2024-10-09 DOI:10.1016/j.radphyschem.2024.112285

Seung-Hwan Oh, Hyun Bin Kim, Jin-Mun Yun, Huisu Kim, Byungnam Kim, Jong-Seok Park

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Abstract

This study demonstrates the synthesis of conjugated 2-(9H-fluoren-7-yl)-9H-fluorene using electron beam irradiation within 3 min in place of the conventional catalytic cross-coupling reactions. 2-bromofluorene was irradiated at various doses (10, 30, 50, 70, 90, and 100 kGy), resulting in the elimination of Br from the 2-position and the formation of C–C bonds between the Br-eliminated fluorenes. The yield of 2-(9H-fluoren-7-yl)-9H-fluorene increased with higher absorbed doses, reaching 65% at 100 kGy. UV–Vis absorption of synthesized 2-(9H-fluoren-7-yl)-9H-fluorene showed an onset at 357 nm and a maximum absorption peak at 325 nm, and blue emission ranging from 340 to 450 nm in photoluminescence (PL). The results of UV–Vis absorption and PL indicated expanded conjugation of 2-(9H-fluoren-7-yl)-9H-fluorene due to the formation of C–C bonds between 2-bromofluorene through the electron beam-induced coupling reaction. Electron beam irradiation offers the potential to significantly reduce the reaction times for synthesis of conjugated organic compounds.

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利用电子束辐照，通过消除 2-溴芴中的 Br，高效合成共轭 2-(9H-芴-7-基)-9H-芴

本研究展示了利用电子束辐照在 3 分钟内合成共轭 2-(9H-芴-7-基)-9H-芴的方法，以取代传统的催化交叉偶联反应。对 2-溴芴进行了不同剂量（10、30、50、70、90 和 100 kGy）的辐照，从而消除了 2 位上的 Br，并在被消除 Br 的芴之间形成了 C-C 键。2-(9H-芴-7-基)-9H-芴的产率随着吸收剂量的增加而增加，在 100 kGy 时达到 65%。合成的 2-(9H-芴-7-基)-9H-芴的紫外可见吸收在 357 nm 处开始，最大吸收峰在 325 nm 处，光致发光（PL）在 340 至 450 nm 处发出蓝色光。紫外可见吸收和光致发光的结果表明，2-（9H-芴-7-基）-9H-芴在电子束诱导的偶联反应中形成了 C-C 键，从而扩大了 2-溴芴的共轭范围。电子束辐照具有显著缩短共轭有机化合物合成反应时间的潜力。

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来源期刊

Radiation Physics and Chemistry 化学-核科学技术

CiteScore

5.60

自引率

17.20%

发文量

574

审稿时长

12 weeks

期刊介绍： Radiation Physics and Chemistry is a multidisciplinary journal that provides a medium for publication of substantial and original papers, reviews, and short communications which focus on research and developments involving ionizing radiation in radiation physics, radiation chemistry and radiation processing. The journal aims to publish papers with significance to an international audience, containing substantial novelty and scientific impact. The Editors reserve the rights to reject, with or without external review, papers that do not meet these criteria. This could include papers that are very similar to previous publications, only with changed target substrates, employed materials, analyzed sites and experimental methods, report results without presenting new insights and/or hypothesis testing, or do not focus on the radiation effects.