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Updated: May 29, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
O,O'-Disubstituted N,N'-dihydroxynaphthalenediimides (DHNDI): first principles designed organic building blocks for
Eric Assen B Kantchev1, Huei Shuan Tan, Tyler B Norsten
1Institute of Materials Research and Engineering, A*STAR, 3 Research Link, Singapore 117602. kantcheveab@imre.a-star.edu.sg
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.
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