O,O′-Disubstituted N,N′-Dihydroxynaphthalenediimides (DHNDI): First Principles Designed Organic Building Blocks for Materials Science

• Published in: Organic letters Vol. 13; no. 20; pp. 5432 - 5435
• Main Authors: Kantchev, Eric Assen B, Tan, Huei Shuan, Norsten, Tyler B, Sullivan, Michael B
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 21.10.2011; Amer Chemical Soc
• Subjects: 1-Naphthylamine - analogs & derivatives; 1-Naphthylamine - chemical synthesis; 1-Naphthylamine - chemistry; Acylation; Alkylation; Chemistry; Chemistry, Organic; Models, Molecular; Molecular Structure; Physical Sciences; Science & Technology; Sulfonic Acids - chemistry; DIIMIDES; SEMICONDUCTOR
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol201906z

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.