Two-step synthesis of a red-emissive warped nanographene derivative via a ten-fold C-H borylation

Kenta Kato; Hsing-An Lin; Motonobu Kuwayama; Mai Nagase; Yasutomo Segawa; Lawrence T Scott; Kenichiro Itami

doi:10.1039/c9sc03061a

Two-step synthesis of a red-emissive warped nanographene derivative via a ten-fold C-H borylation

Chem Sci. 2019 Aug 9;10(39):9038-9041. doi: 10.1039/c9sc03061a. eCollection 2019 Oct 21.

Authors

Kenta Kato¹, Hsing-An Lin^{1

2}, Motonobu Kuwayama^{1

2

3}, Mai Nagase¹, Yasutomo Segawa^{1

2}, Lawrence T Scott⁴, Kenichiro Itami^{1

2

3}

Affiliations

¹ Graduate School of Science , Nagoya University , Chikusa , Nagoya , 464-8602 , Japan . Email: Itami@chem.nagoya-u.ac.jp ; Email: ysegawa@nagoya-u.jp.
² JST-ERATO , Itami Molecular Nanocarbon Project , Nagoya University , Chikusa , Nagoya , 464-8602 , Japan.
³ Institute of Transformative Bio-Molecules (WPI-ITbM) , Nagoya University , Chikusa , Nagoya , 464-8602 , Japan.
⁴ Department of Chemistry , University of Nevada , Reno , NV 89557-0216 , USA.

Abstract

The regioselective ten-fold borylation of warped nanographene (WNG: C₈₀H₃₀) was achieved by modifying the reaction conditions of a previously reported Ir-catalyzed C-H borylation, affording decaborylated WNG in high yield (75%) from pristine WNG. The solid-state structure of decaborylated WNG was confirmed by X-ray crystallography. Corresponding decaarylated WNGs containing electron-withdrawing and -donating groups were synthesized from decaborylated WNG using Suzuki-Miyaura cross-coupling reactions to afford the red-emissive warped nanographene derivative.