LAUSR.org creates dashboard-style pages of related content for over 1.5 million academic articles. Sign Up to like articles & get recommendations!

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

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… Click to show full 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.

Keywords: modulation dihydroxynaphthalenediimide; induced color; deprotonation induced; deprotonation; dihydroxynaphthalenediimide based; color modulation

Journal Title: ChemPlusChem
Year Published: 2023

Link to full text (if available)


Share on Social Media:                               Sign Up to like & get
recommendations!

Related content

More Information              News              Social Media              Video              Recommended



                Click one of the above tabs to view related content.