TY - JOUR
T1 - Tetrakis(phenylethynyl)tetracene
T2 - A New π-Extended Rubrene Derivative
AU - Kitamura, Kei
AU - Asahina, Kenta
AU - Nagai, Yusaku
AU - Sugiyama, Haruki
AU - Uekusa, Hidehiro
AU - Hamura, Toshiyuki
N1 - Funding Information:
This work was supported by JSPS KAKENHI Grant Number JP15H05840 in Middle Molecular Strategy and JST ACT-C Grant Number JPMJCR12YY, Japan.
Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/9/20
Y1 - 2018/9/20
N2 - An efficient synthetic route to 5,6,11,12-tetrakis(arylethynyl)tetracenes, new π-extended rubrene derivatives, was developed by means of [2+4] cycloaddition of dialkynylnaphthalyne and dialkynylisobenzofuran. Importantly, two alkynyl groups introduced into the aryne exerts a significant effect in lowering the LUMO energy, allowing practical access to sterically overcrowded polycyclic structures through an efficient HOMO–LUMO interaction. Study on the potential reactivity inherent in the peri-ethynyl-substituted tetracenes revealed several interesting reactivities. X-ray analysis of these new π-extended derivatives showed distorted structures to reduce steric repulsion due to the existence of the substituents at the peri-positions.
AB - An efficient synthetic route to 5,6,11,12-tetrakis(arylethynyl)tetracenes, new π-extended rubrene derivatives, was developed by means of [2+4] cycloaddition of dialkynylnaphthalyne and dialkynylisobenzofuran. Importantly, two alkynyl groups introduced into the aryne exerts a significant effect in lowering the LUMO energy, allowing practical access to sterically overcrowded polycyclic structures through an efficient HOMO–LUMO interaction. Study on the potential reactivity inherent in the peri-ethynyl-substituted tetracenes revealed several interesting reactivities. X-ray analysis of these new π-extended derivatives showed distorted structures to reduce steric repulsion due to the existence of the substituents at the peri-positions.
KW - crowded tetracene
KW - cycloaddition
KW - dialkynylisobenzofuran
KW - naphthalyne
KW - polycycles
KW - rubrene
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U2 - 10.1002/chem.201803294
DO - 10.1002/chem.201803294
M3 - Article
C2 - 30070763
AN - SCOPUS:85053555015
SN - 0947-6539
VL - 24
SP - 14034
EP - 14038
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 53
ER -