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Deprotonation-Induced Color Modulation in N,N'-Dihydroxynaphthalenediimide-Based Organic Crystals.
- Source :
-
ChemPlusChem [Chempluschem] 2023 Jul; Vol. 88 (7), pp. e202300140. Date of Electronic Publication: 2023 Apr 13. - Publication Year :
- 2023
-
Abstract
- N,N'-dihydroxy-1,4,5,8-naphthalenetetracarboxdiimide (NDI-(OH) <subscript>2</subscript> ) has attracted much attention in recent years, because its doubly deprotonated state, (O-NDI-O) <superscript>2-</superscript> , has metal-coordination ability and characteristic electronic transition useful for designing electronic and optical functions. In contrast, a molecular crystal with the mono-deprotonated (HO-NDI-O) <superscript>-</superscript> ion remains unknown. We herein report an organic crystal containing non-disproportionated (HO-NDI-O) <superscript>-</superscript> ions, which are connected by very strong O-H-O hydrogen bonds. Its lowest energy absorption band (450 to 650 nm) is observed in between that of NDI-(OH) <subscript>2</subscript> (380 nm) and isolated (O-NDI-O) <superscript>2-</superscript> (500 to 850 nm) species, consistent with the molecular orbital calculations. This absorption originates from the electronic transition from deprotonated imide-based orbitals to NDI-core orbitals, which can be influenced by the hydrogen bonds around imide group. Consequently, the optical properties of NDI-(OH) <subscript>2</subscript> can be modulated by the stepwise deprotonation and hydrogen-bonding interactions.<br /> (© 2023 Wiley-VCH GmbH.)
Details
- Language :
- English
- ISSN :
- 2192-6506
- Volume :
- 88
- Issue :
- 7
- Database :
- MEDLINE
- Journal :
- ChemPlusChem
- Publication Type :
- Academic Journal
- Accession number :
- 36973181
- Full Text :
- https://doi.org/10.1002/cplu.202300140