Tuning the NIR Absorption Properties of 1,3,4,6,9b‐Pentaazaphenalene Derivatives Through the Spatially Separated Frontier Molecular Orbitals
Strategical modulation of energy levels of molecular electronic orbitals and resulting near‐infrared (NIR) absorption properties of 2,5,7,9‐tetrasubstituted 1,3,4,6,9b‐pentaazaphenalene (5AP) derivatives are reported. Recent reports on NIR‐absorbing materials mainly rely on donor–acceptor electronic...
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| Published in | European journal of organic chemistry Vol. 2020; no. 7; pp. 777 - 783 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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21.02.2020
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| Abstract | Strategical modulation of energy levels of molecular electronic orbitals and resulting near‐infrared (NIR) absorption properties of 2,5,7,9‐tetrasubstituted 1,3,4,6,9b‐pentaazaphenalene (5AP) derivatives are reported. Recent reports on NIR‐absorbing materials mainly rely on donor–acceptor electronic interactions or macrocyclic π‐conjugated systems. We achieved the narrow HOMO–LUMO gap based on spatially separated frontier molecular orbitals (FMOs) of 5APs. The FMOs of 5APs enabled us to selectively tune either their HOMO or LUMO by choosing the position of the substituent.
Judicious modification of substituents on a 1,3,4,6,9b‐pentaazaphenalene scaffold resulted in NIR absorption materials. The spatially separated frontier molecular orbitals enabled independent tuning of their energy levels toward NIR absorption properties. |
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| AbstractList | Strategical modulation of energy levels of molecular electronic orbitals and resulting near‐infrared (NIR) absorption properties of 2,5,7,9‐tetrasubstituted 1,3,4,6,9b‐pentaazaphenalene (5AP) derivatives are reported. Recent reports on NIR‐absorbing materials mainly rely on donor–acceptor electronic interactions or macrocyclic π‐conjugated systems. We achieved the narrow HOMO–LUMO gap based on spatially separated frontier molecular orbitals (FMOs) of 5APs. The FMOs of 5APs enabled us to selectively tune either their HOMO or LUMO by choosing the position of the substituent. Strategical modulation of energy levels of molecular electronic orbitals and resulting near‐infrared (NIR) absorption properties of 2,5,7,9‐tetrasubstituted 1,3,4,6,9b‐pentaazaphenalene (5AP) derivatives are reported. Recent reports on NIR‐absorbing materials mainly rely on donor–acceptor electronic interactions or macrocyclic π‐conjugated systems. We achieved the narrow HOMO–LUMO gap based on spatially separated frontier molecular orbitals (FMOs) of 5APs. The FMOs of 5APs enabled us to selectively tune either their HOMO or LUMO by choosing the position of the substituent. Judicious modification of substituents on a 1,3,4,6,9b‐pentaazaphenalene scaffold resulted in NIR absorption materials. The spatially separated frontier molecular orbitals enabled independent tuning of their energy levels toward NIR absorption properties. Strategical modulation of energy levels of molecular electronic orbitals and resulting near-infrared (NIR) absorption properties of 2,5,7,9-tetrasubstituted 1,3,4,6,9b-pentaazaphenalene (5AP) derivatives are reported. Recent reports on NIR-absorbing materials mainly rely on donor-acceptor electronic interactions or macrocyclic pi-conjugated systems. We achieved the narrow HOMO-LUMO gap based on spatially separated frontier molecular orbitals (FMOs) of 5APs. The FMOs of 5APs enabled us to selectively tune either their HOMO or LUMO by choosing the position of the substituent. |
| Author | Chujo, Yoshiki Watanabe, Hiroyuki Ochi, Junki Tanaka, Kazuo |
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| Keywords | Heterocycles POLYMERS Azaphenalene SOLAR-CELLS FLUOROPHORES PERFORMANCE AZULENE PHOTOPHYSICAL PROPERTIES TERAZULENE Fused-ring systems Near infrared |
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| SubjectTerms | Absorption Azaphenalene Chemistry Chemistry, Organic Derivatives Electrons Energy levels Fused‐ring systems Heterocycles Molecular orbitals Near infrared Physical Sciences Science & Technology |
| Title | Tuning the NIR Absorption Properties of 1,3,4,6,9b‐Pentaazaphenalene Derivatives Through the Spatially Separated Frontier Molecular Orbitals |
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