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 in | Chemical communications (Cambridge, England) Vol. 53; no. 36; pp. 5036 - 5039 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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Royal Soc Chemistry
02.05.2017
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| Abstract | 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. |
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| AbstractList | 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. 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. |
| Author | Chujo, Yoshiki Watanabe, Hiroyuki Tanaka, Kazuo Hirose, Masataka |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28428996$$D View this record in MEDLINE/PubMed |
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| Keywords | 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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| Snippet | This communication describes the transformation of a non-emissive heterocycle into a luminophore via modulation of molecular orbitals by employing a... This communication describes the transformation of a non-emissive heterocycle into a luminophore via modulation of molecular orbitals by employing a... |
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| Title | Development of emissive aminopentaazaphenalene derivatives employing a design strategy for obtaining luminescent conjugated molecules by modulating the symmetry of molecular orbitals with substituent effects |
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