title: Synthesis and structure-property relationships of phthalimide and naphthalimide based organic π-conjugated small molecules.
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.
authors.affiliation: Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, Canada T2N 1N4. greogry.welch@ucalgary.ca.
authors.forename: Abby-Jo
authors.initials: AJ
authors.lastname: Payne
authors.forename: Arthur D
authors.initials: AD
authors.lastname: Hendsbee
authors.forename: Seth M
authors.initials: SM
authors.lastname: McAfee
authors.forename: Devproshad K
authors.initials: DK
authors.lastname: Paul
authors.forename: Kunal
authors.initials: K
authors.lastname: Karan
authors.forename: Gregory C
authors.initials: GC
authors.lastname: Welch