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Issue 21, 2016
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Synthesis and structure–property relationships of phthalimide and naphthalimide based organic π-conjugated small molecules

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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.

Graphical abstract: Synthesis and structure–property relationships of phthalimide and naphthalimide based organic π-conjugated small molecules

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Article information


Submitted
08 Mar 2016
Accepted
07 May 2016
First published
10 May 2016

This article is Open Access

Phys. Chem. Chem. Phys., 2016,18, 14709-14719
Article type
Paper
Author version available

Synthesis and structure–property relationships of phthalimide and naphthalimide based organic π-conjugated small molecules

A. Payne, A. D. Hendsbee, S. M. McAfee, D. K. Paul, K. Karan and G. C. Welch, Phys. Chem. Chem. Phys., 2016, 18, 14709
DOI: 10.1039/C6CP01596D

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