Journal
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
Volume 18, Issue 21, Pages 14709-14719Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cp01596d
Keywords
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Funding
- Canada Research Chairs Program
- Natural Science and Engineering Council of Canada [NSERC RGPIN 435715-2013]
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Five organic pi-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 octylnaphthatimide 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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