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

Research output: Contribution to journalArticle

97 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2728-2733
Number of pages6
JournalJournal of the American Chemical Society
Volume139
Issue number7
DOIs
Publication statusPublished - 2017 Feb 22

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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