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Updated: Jun 5, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
N,N'-Dicyclo-hexyl-naphthalene-1,8;4:5-dicarboximide
Deepak Shukla1, Manju Rajeswaran
1Eastman Kodak Company, Kodak Research Laboratories, Rochester, NY 14650-2106, USA.
Abstract:
The title compound, C(26)H(26)N(2)O(4), synthesized by the reaction of naphthalene-1,4,5,8-tetra-carboxylic acid anhydride and cyclo-hexyl-amine, exhibits good n-type semiconducting properties. Accordingly, thin-film transistor devices comprising this compound show n-type behavior with high field-effect electron moblity ca 6 cm(2)/Vs [Shukla, Nelson, Freeman, Rajeswaran, Ahearn, Meyer & Carey(2008 ▶). Chem. Mater. Submitted]. The asymmetric unit comprises one-quarter of the centrosymmetric mol-ecule in which all but two methyl-ene C atoms of the cyclo-hexane ring lie on a mirror plane; the point-group symmetry is 2/m. The naphthalene-diimide unit is strictly planar, and the cyclo-hexane rings adopt chair conformations with the diimide unit in an equatorial position on each ring.
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