title: O,O'-Disubstituted N,N'-dihydroxynaphthalenediimides (DHNDI): first principles designed organic building blocks for materials science.
abstract: N,N'-Disubstituted naphthalenediimides (NDIs), planar, electron-deficient building blocks, play an important role in materials and biological sciences. Naphthalene core substituents control the HOMO and LUMO energies, whereas the N-alkyl or aryl substituents affect the solubility, aggregation, and packing propensity in condensed phases. N,N'-Dihydroxynaphthalenediimide (DHNDI) allows expanding the chemical diversity by O-alkylation, acylation, or sulfonylation; these derivatives also allow fine-tuning of the HOMO/LUMO levels. The synthesis, UV-vis, electrochemical, solid state, and computational prediction of the properties of such derivatives are presented.
authors.affiliation: Institute of Materials Research and Engineering, A*STAR, 3 Research Link, Singapore 117602. kantcheveab@imre.a-star.edu.sg
authors.forename: Eric Assen B
authors.initials: EA
authors.lastname: Kantchev
authors.forename: Huei Shuan
authors.initials: HS
authors.lastname: Tan
authors.forename: Tyler B
authors.initials: TB
authors.lastname: Norsten
authors.forename: Michael B
authors.initials: MB
authors.lastname: Sullivan
mesh_terms: D015057:1-Naphthylamine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D000215:Acylation; D000478:Alkylation; D008958:Models, Molecular; D015394:Molecular Structure; D013451:Sulfonic Acids / Q000737:chemistry
chemical_list: D013451:Sulfonic Acids; D015057:1-Naphthylamine