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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.
A new organic semiconductor synthesized from naphthalene-1,4,5,8-tetra-carboxylic acid anhydride and cyclohexylamine shows promising n-type semiconducting properties. Thin-film transistors made with this compound exhibit high electron mobility, suitable for electronic applications.
Area of Science:
- Organic electronics
- Materials science
- Solid-state chemistry
Background:
- Naphthalene-diimide derivatives are explored for organic semiconductor applications.
- Developing efficient n-type organic semiconductors is crucial for complementary circuits.
Purpose of the Study:
- To synthesize and characterize a novel organic compound for n-type semiconducting applications.
- To evaluate the performance of thin-film transistors based on the synthesized compound.
Main Methods:
- Synthesis via reaction of naphthalene-1,4,5,8-tetra-carboxylic acid anhydride and cyclohexylamine.
- Fabrication and testing of thin-film transistor devices.
- Crystallographic analysis of the compound's molecular structure.
Main Results:
- The synthesized compound C(26)H(26)N(2)O(4) exhibits good n-type semiconducting properties.
- Thin-film transistors demonstrated n-type behavior with high field-effect electron mobility (approx. 6 cm(2)/Vs).
- Crystallographic data revealed a centrosymmetric molecule with planar naphthalene-diimide and chair-conformation cyclohexane units.
Conclusions:
- The novel naphthalene-diimide derivative is a promising n-type organic semiconductor.
- The high electron mobility suggests potential for use in organic electronic devices.
- Molecular structure correlates with observed semiconducting properties.
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