Abstract
N,N’-dihydroxy-1,4,5,8-naphthalenetetracarboxdiimide (NDI−(OH)2) has attracted much attention in recent years, because its doubly deprotonated state, (O−NDI−O)2−, 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)− ion remains unknown. We herein report an organic crystal containing non-disproportionated (HO−NDI−O)− 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)2 (380 nm) and isolated (O−NDI−O)2− (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)2 can be modulated by the stepwise deprotonation and hydrogen-bonding interactions.
Original language | English |
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Article number | e202300140 |
Journal | ChemPlusChem |
Volume | 88 |
Issue number | 7 |
DOIs | |
Publication status | Published - 2023 Jul |
Keywords
- chromophores
- crystal engineering
- deprotonation
- hydrogen bonds
- naphthalenediimide
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Tohoku University Reports Findings in Science (Deprotonation-Induced Color Modulation in N,N'-Dihydroxynaphthalenediimide-Based Organic Crystals)
23/4/21
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