Journal
LANGMUIR
Volume 31, Issue 45, Pages 12408-12416Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.langmuir.5b03295
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Funding
- National Science Foundation [CHE1058241]
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Side chains containing two diacetylene units spaced by an odd number of methylene units exhibit pronounced bumps composed of 0.3 nm steps, in opposite directions, at odd and even side-chain positions. In densely packed self-assembled monolayers, the bis-diacetylene bumps stack into each other, similar to the stacking of paper cups. Bis-diacetylene side chain structure and associated packing constraints can be tailored by altering the bump width, direction, side-chain location, and overall side-chain length as a means to direct the identities and alignments of adjacent molecules within monolayers. Scanning tunneling microscopy (STM) at the solution-HOPG interface confirms the high selectivity and fidelity with which bis-diacetylene bump stacking directs the packing of shape-complementary side chains within one-component monolayers and within two-component, 1-D self-patterned monolayers. Drop cast or moderately annealed monolayers of anthracenes bearing two bis-diacetylene side chains assemble single domains as large as 10(5) nm(2). Light-induced cross-linking of two-component, 1-D patterned monolayers generates linear polydiacetylene alternating copolymers (A-B-)(x) and 2-D grid polydiacetylene alternating copolymers (A(-B-)(-B-)A(-B-)(-B-))(x) that covalently lock in monolayer structure and patterns.
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