TY - JOUR
T1 - Unveiling a New Aspect of Simple Arylboronic Esters
T2 - Long-Lived Room-Temperature Phosphorescence from Heavy-Atom-Free Molecules
AU - Shoji, Yoshiaki
AU - Ikabata, Yasuhiro
AU - Wang, Qi
AU - Nemoto, Daisuke
AU - Sakamoto, Atsushi
AU - Tanaka, Naoki
AU - Seino, Junji
AU - Nakai, Hiromi
AU - Fukushima, Takanori
N1 - Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/2/22
Y1 - 2017/2/22
N2 - 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.
AB - 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.
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U2 - 10.1021/jacs.6b11984
DO - 10.1021/jacs.6b11984
M3 - Article
C2 - 28135418
AN - SCOPUS:85013419019
SN - 0002-7863
VL - 139
SP - 2728
EP - 2733
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 7
ER -