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Self-Assembling Functionalizable Polydiacetylenes and their Optical Properties

Published online by Cambridge University Press:  10 February 2011

M. Sukwattanasinitt,
X. Wang,
D-C. Lee,
L. Li,
J. Kumar,
S. K. Tripathy and
D. J. Sandman
M. Sukwattanasinitt
Affiliation:
Center for Advanced Materials and Department of Chemistry and Massachusetts 01854–2881
X. Wang
Affiliation:
Center for Advanced Materials and Department of Chemistry and Massachusetts 01854–2881
D-C. Lee
Affiliation:
Center for Advanced Materials and Department of Chemistry and Massachusetts 01854–2881
L. Li
Affiliation:
Physics and Applied Physics, University of Massachusetts Lowell, Lowell, Massachusetts 01854–2881
J. Kumar
Affiliation:
Physics and Applied Physics, University of Massachusetts Lowell, Lowell, Massachusetts 01854–2881
S. K. Tripathy
Affiliation:
Center for Advanced Materials and Department of Chemistry and Massachusetts 01854–2881
D. J. Sandman
Affiliation:
Center for Advanced Materials and Department of Chemistry and Massachusetts 01854–2881
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Abstract

The alkoxycarbonylmethylurethanes of 9-(N-methyl-N-phenylamino)-5,7-nonadiyn-l-ol were synthesized and polymerized by 60Co gamma radiation. The resulting polydiacetylenes (PDA) are soluble, processable, and self-assemble into an acentric array. These PDAs are susceptible to postpolymerization functionalization via its dialkylaniline and ester groups, and hence comprise the most versatile PDA system for systematic chemical modification reported to date. Dialkylaniline functionalization via tetracyanoethylene and diazonium salt coupling led, respectively, to materials with interesting second order nonlinear optical properties and that exhibit directly photofabricated regular surface relief gratings. The latter materials provide the first example of a rigid rod polymer (lacking a detectable glass transition) to exhibit such phenomena. Moreover, these PDAs can form self-assembled multilayer structure in water by ester hydrolysis.

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