Details

Autor(en) / Beteiligte

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

Titel

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

Ist Teil von

• Nature communications, 2023-08, Vol.14 (1), p.5248-5248, Article 5248

Ort / Verlag

London: Nature Publishing Group

Erscheinungsjahr

2023

Quelle

Free E-Journal (出版社公開部分のみ）

Beschreibungen/Notizen

• 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).