Synthesis and tunable chiroptical properties of chiral BODIPY-based D–π–A conjugated polymers?

Journal of Materials Chemistry C Pub Date: 2013-11-12 DOI: 10.1039/C3TC32029D

Abstract

Three novel donor–π–acceptor (D–π–A) type chiral polymers P1, P2, and P3 could be synthesized from diiodo-substituted chiral boron-dipyrromethene (BODIPY) derivative (M-1) with 2,7-diethynyl-9,9-dioctyl-9H-fluorene (M-2), 3,6-diethynyl-9-octyl-9H-carbazole (M-3), and 3,7-diethynyl-10-dodecyl-10H-phenothiazine (M-4) via a Pd-catalyzed Sonogashira coupling reaction, respectively. From the choice of the three different donor structures, the three chiral BODIPY-based conjugated polymers can exhibit a red fluorescent emission centered at around 624–650 nm, with tunable band gaps in the range 1.56–1.96 eV, respectively. Interestingly, compared with the anisotropy (r = 0.005) and the CPL dissymmetry factor (glum < 0.01) of the chiral BODIPY small molecule as the counterpart, the three chiral polymers can exhibit a high r (up to 0.10 for P1) and a large glum (up to 0.32 for P2), which can be attributed to the interchain π–π stacking effect and the well-defined chiral arrangement along these polymers backbone.

Graphical abstract: Synthesis and tunable chiroptical properties of chiral BODIPY-based D–π–A conjugated polymers
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