Deep-red emissive conjugated poly(2,6-BODIPY-ethynylene)s bearing alkyl side chains

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Novel deep-red emissive poly(2,6-BODIPY-ethynylene)s bearing dodecyl side chains (polymers A, B, and C) have been prepared by palladium-catalyzed Sonogashira polymerization of 2,6-diiodo-functionalized BODIPY monomers with 2,6-diethynyl-functionalized BODIPY monomers. These polymers emit in the deep-red region with emission maxima at up to 690 nm, and exhibit significant red shifts (up to 166 and 179 nm) of both absorption and emission maxima compared with their parent BODIPY dyes due to significant extension of π-conjugation. These polymers possess good thermal stability with decomposition temperature between 270 and 360°C. The polymers exhibit a little larger Stokes shifts and shorter lifetime than their corresponding BODIPY dyes. The solid state thin films of polymers A, B, and C emit in near-infrared region between 723 and 743 nm, and show significantly red shifts (up to 57 nm) in absorption and emission maxima relative to their polymer solution. © 2009 Wiley Periodicals, Inc.

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Journal of Polymer Science, Part A: Polymer Chemistry