Unveiling a New Aspect of Simple Arylboronic Esters: Long-Lived Room-Temperature Phosphorescence from Heavy-Atom-Free Molecules

Yoshiaki Shoji, Yasuhiro Ikabata, Qi Wang, Daisuke Nemoto, Atsushi Sakamoto, Naoki Tanaka, Junji Seino, Hiromi Nakai*, Takanori Fukushima

*この研究の対応する著者

研究成果: Article査読

141 被引用数 (Scopus)

抄録

Arylboronic esters can be used as versatile reagents in organic synthesis, as represented by Suzuki-Miyaura cross-coupling. Here we report a serendipitous finding that simple arylboronic esters are phosphorescent in the solid state at room temperature with a lifetime on the order of several seconds. The phosphorescence properties of arylboronic esters are remarkable in light of the general notion that phosphorescent organic molecules require heavy atoms and/or carbonyl groups for the efficient generation of a triplet excited state. Theoretical calculations on phenylboronic acid pinacol ester indicated that this molecule undergoes an out-of-plane distortion at the (pinacol)B-Cipso moiety in the T1 excited state, which is responsible for its phosphorescence. A compound survey with 19 arylboron compounds suggested that the phosphorescence properties might be determined by solid-state molecular packing rather than by the patterns and numbers of boron substituents on the aryl units. The present finding may update the general notion of phosphorescent organic molecules.

本文言語English
ページ(範囲)2728-2733
ページ数6
ジャーナルJournal of the American Chemical Society
139
7
DOI
出版ステータスPublished - 2017 2 22

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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