Development of emissive aminopentaazaphenalene derivatives employing a design strategy for obtaining luminescent conjugated molecules by modulating the symmetry of molecular orbitals with substituent effects

This communication describes the transformation of a non-emissive heterocycle into a luminophore via modulation of molecular orbitals by employing a dialkylamine-substituted pentaazaphenalene (A5AP) skeleton. It was presumed that the introduction of the amine group changed the symmetry-forbidden HOM...

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Published inChemical communications (Cambridge, England) Vol. 53; no. 36; pp. 5036 - 5039
Main Authors Watanabe, Hiroyuki, Hirose, Masataka, Tanaka, Kazuo, Chujo, Yoshiki
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 02.05.2017
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
POLYMERS
BODIPY
STATES
SPIN
CHEMISTRY
CRYSTAL-STRUCTURES
2,5,8-TRI-TERT-BUTYL-1,3-DIAZAPHENALENYL
COORDINATION
S-TRIAZINO HETEROCYCLES
1,3,4,6,9B-PENTAAZAPHENALENES
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Summary:This communication describes the transformation of a non-emissive heterocycle into a luminophore via modulation of molecular orbitals by employing a dialkylamine-substituted pentaazaphenalene (A5AP) skeleton. It was presumed that the introduction of the amine group changed the symmetry-forbidden HOMO-LUMO (H-L) transition to an allowed one. According to optical measurements and theoretical calculations, the H-L transition was turned into the symmetry-allowed one because of the lone pair on the nitrogen atom in the dialkylamine substituent. Finally, the A5AP derivatives presented significant emission from the H-L transition.
Bibliography:KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc01287j