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 () and Yao-Ting Wu ()
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Hao-Wen Kang: National Cheng Kung University
Yu-Chiao Liu: Institute of Chemistry, Academia Sinica
Wei-Kai Shao: National Cheng Kung University
Yu-Chen Wei: National Taiwan University
Chi-Tien Hsieh: National Cheng Kung University
Bo-Han Chen: National Tsing Hua University
Chih-Hsuan Lu: National Tsing Hua University
Shang-Da Yang: National Tsing Hua University
Mu-Jeng Cheng: National Cheng Kung University
Pi-Tai Chou: National Taiwan University
Ming-Hsi Chiang: Institute of Chemistry, Academia Sinica
Yao-Ting Wu: National Cheng Kung University

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract 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).

Date: 2023
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DOI: 10.1038/s41467-023-40990-8

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