Synthesis, structural analysis, and properties of highly twisted alkenes 13,13’-bis(dibenzo[a,i]fluorenylidene) and its derivatives

Hao Wen Kang, Yu Chiao Liu, Wei Kai Shao, Yu Chen Wei, Chi Tien Hsieh, Bo Han Chen, Chih Hsuan Lu, Shang Da Yang, Mu Jeng Cheng, Pi Tai Chou, Ming Hsi Chiang, Yao Ting Wu

研究成果: Article同行評審

2 引文 斯高帕斯(Scopus)

摘要

The rotation of a C = C bond in an alkene can be efficiently accelerated by creating the high-strain ground state and stabilizing the transition state of the process. Herein, the synthesis, structures, and properties of several highly twisted alkenes are comprehensively explored. A facile and practical synthetic approach to target molecules is developed. The twist angles and lengths of the central C = C bonds in these molecules are 36–58° and 1.40–1.43 Å, respectively, and confirmed by X-ray crystallography and DFT calculations. A quasi-planar molecular half with the π-extended substituents delivers a shallow rotational barrier (down to 2.35 kcal/mol), indicating that the rotation of the C = C bond is as facile as that of the aryl-aryl bond in 2-flourobiphenyl. Other versatile and unique properties of the studied compounds include a broad photoabsorption range (from 250 up to 1100 nm), a reduced HOMO-LUMO gap (1.26–1.68 eV), and a small singlet-triplet energy gap (3.65–5.68 kcal/mol).

原文English
文章編號5248
期刊Nature communications
14
發行號1
DOIs
出版狀態Published - 2023 12月

All Science Journal Classification (ASJC) codes

  • 一般化學
  • 一般生物化學,遺傳學和分子生物學
  • 一般物理與天文學

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