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Updated: Mar 21, 2026

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Synthesis and structure-property relationships of phthalimide and naphthalimide based organic π-conjugated small
Abby-Jo Payne1, Arthur D Hendsbee, Seth M McAfee
1Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, Canada T2N 1N4. greogry.welch@ucalgary.ca.
Abstract:
Five organic π-conjugated small molecules with bithiophene-phthalimide backbones bearing alkyl chains of different symmetry, length and branching character were synthesized using optimized microwave and direct heteroarylation protocols. The chosen alkyl chains were 1-ethylpropyl, 1-methylbutyl, pentyl, hexyl and octyl. A sixth compound was also synthesized replacing the phthalimide terminal units with octylnaphthalimide for additional scope. Through the thorough analysis of both thermal and optical properties and the investigation of self-assembly tendencies by single crystal X-ray diffraction and variable angle spectroscopic ellipsometry it is evident that alkyl side chains and building block size influence many facets of material properties. Within this class of materials the 1-ethylpropyl derivative exhibited the most unique behaviour.
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