Soluble poly(diacetylene)s using the perfluorophenyl-phenyl motif as a supramolecular synthon.
A series of diacetylene monomers with benzoyl, 4-hexylbenzoyl, 4-dodecylbenzoyl, and perfluorobenzoyl substituents were synthesized and investigated with respect to their crystal structures and polymerizability. In the absence of perfluorophenyl-phenyl interactions, the crystal structures of related alkylated and nonalkylated derivatives were substantially different and dominated by the phase segregation between the alkylated side chains and the diaryl-substituted diacetylene cores. By contrast, the perfluorophenyl-phenyl interactions served as a reliable supramolecular synthon in that they persisted in the crystal structures of different alkylated and nonalkylated derivatives. The packing of the diacetylene functions was appropriate for a topochemical polymerization in these cases, and the perfluorophenyl-phenyl interaction determined the polymerization direction. As a result, soluble alternating diacetylene copolymers were obtained which were further characterized with solution phase methods.
Xu
Rui
R
Department of Materials, ETH Zürich, Wolfgang-Pauli-Strasse 10, HCI H515, CH-8093 Zürich, Switzerland.
Schweizer
W Bernd
WB
Frauenrath
Holger
H
D000114:Acetylene / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D000473:Alkanes / Q000737:chemistry; D000478:Alkylation; D019817:Benzoic Acid / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D000078789:Polyacetylene Polymer; D011108:Polymers / Q000138:chemical synthesis*; D053279:Polyynes / Q000138:chemical synthesis*; D012995:Solubility; D012996:Solutions / Q000737:chemistry; D014961:X-Ray Diffraction
D000473:Alkanes; D006845:Hydrocarbons, Fluorinated; D000078789:Polyacetylene Polymer; D011108:Polymers; D012996:Solutions; D053279:Polyynes; C082361:polydiacetylene; D019817:Benzoic Acid; D000114:Acetylene