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O,O'-Disubstituted N,N'-Dihydroxynaphthalenediimides (DHNDI): First Principles Designed Organic Building Blocks for Materials Science
Eric Assen B. Kantchev, Huei Shuan Tan, Tyler B. Norsten, and Michael B. Sullivan
Institute of Materials Research and Engineering, A*STAR, 3 Research Link, Singapore 117602, and Institute of High Performance Computing, A*STAR, 1 Fusionopolis Way #16-16, The Connexis, Singapore 138632
Publication Date (Web): September 22, 2011
Org. Lett., 2011, 13 5432-5435.
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.
DOI: 10.1021/ol201906z