Doubly linked chiral phenanthrene oligomers for homogeneously π-extended helicenes with large effective conjugation length

Yusuke Nakakuki, Takashi Hirose (), Hikaru Sotome, Min Gao, Daiki Shimizu, Ruiji Li, Jun-ya Hasegawa, Hiroshi Miyasaka and Kenji Matsuda ()
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Yusuke Nakakuki: Kyoto University
Takashi Hirose: Kyoto University
Hikaru Sotome: Osaka University
Min Gao: Hokkaido University
Daiki Shimizu: Kyoto University
Ruiji Li: Kyoto University
Jun-ya Hasegawa: Hokkaido University
Hiroshi Miyasaka: Osaka University
Kenji Matsuda: Kyoto University

Nature Communications, 2022, vol. 13, issue 1, 1-10

Abstract: Abstract Helically twisted conductive nanocarbon materials are applicable to optoelectronic and electromagnetic molecular devices working on the nanometer scale. Herein, we report the synthesis of per-peri-perbenzo[5]- and [9]helicenes in addition to previously reported π-extended [7]helicene. The homogeneously π-extended helicenes can be regarded as helically fused oligo-phenanthrenes. The HOMO−LUMO gap decreased significantly from 2.14 to 1.15 eV with increasing helical length, suggesting the large effective conjugation length (ECL) of the π-extended helical framework. The large ECL of π-extended helicenes is attributed to the large orbital interactions between the phenanthrene subunits at the 9- and 10-positions, which form a polyene-like electronic structure. Based on the experimental results and DFT calculations, the ultrafast decay dynamics on the sub-picosecond timescale were attributed to the low-lying conical intersection.

Date: 2022
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DOI: 10.1038/s41467-022-29108-8

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