Deprotonation-Induced Color Modulation in N,N′-Dihydroxynaphthalenediimide-Based Organic Crystals

Tappei Tanabe, Tetsu Sato, Kentaro Fuku, Shinya Takaishi, Hiroaki Iguchi

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

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 languageEnglish
Article numbere202300140
JournalChemPlusChem
Volume88
Issue number7
DOIs
Publication statusPublished - 2023 Jul

Keywords

  • chromophores
  • crystal engineering
  • deprotonation
  • hydrogen bonds
  • naphthalenediimide

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