NDLI: Poly(thiophenylanilino) and poly(furanylanilino) polymers

Content Provider	Springer Nature Link
Author	Baldwin, Lawrence C. Chafin, Andrew P. Deschamps, Jeffrey R. Hawkins, Samantha A. Wright, Michael E. Witker, David L. Prokopuk, Nicholas
Copyright Year	2008
Abstract	Novel hybrid polymers with thiophenylanilino and furanylanilino backbones and substituted phenyl side groups are reported. The new monomers bis-(4-heterocyclic-2-yl-phenyl)-aryl-amine (heterocyclic = thiophen with aryl = 4-benzoyl (2a), 4-nitro-phenyl (2b) and furan with aryl = 4-benzoyl-phenyl (3a), 4-nitro-phenyl (3b)) were prepared by monosubstituting triphenylamine under electrophilic aromatic conditions affording 4-nitrotriphenylamine and 4-benzoyltriphenylamine. Di(bromination) of the latter compounds followed by Stille cross-coupling reactions with 2-tributylstannylthiophene or 2-tributylstannylfuran produces the new monomers 2a–b and 3a–b in high yield. The monomers are electrochemically polymerized at relatively low potentials (<0.8 V versus Ag$^{+}$/AgCl) in acetonitrile electrolytes resulting in electroactive films. All the new polymers can be repeatedly oxidized and reduced with little loss of electrochemical activity. Vibrational spectroscopy reveals that the monomer units are connected predominately via coupling of the thiophenyl or furanyl rings yielding the novel polymers. Single-crystal molecular structure determinations of 4-nitrotriphenylamine and monomer 3b indicate the importance of the electron-withdrawing groups on the pendent phenyl groups in determining the extent of delocalization of the extended multi-ring systems. Molecular orbital calculations suggest that the HOMO of 2b is delocalized about both anilino and thiophenyl portions of the molecule.
Starting Page	4182
Ending Page	4191
Page Count	10
File Format	PDF
ISSN	00222461
Journal	Journal of Materials Science
Volume Number	43
Issue Number	12
e-ISSN	15734803
Language	English
Publisher	Springer US
Publisher Date	2008-04-23
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Mechanics Crystallography Continuum Mechanics and Mechanics of Materials Polymer Sciences Characterization and Evaluation of Materials Materials Science
Content Type	Text
Resource Type	Article
Subject	Ceramics and Composites Mechanics of Materials Mechanical Engineering Polymers and Plastics

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