Synthesis, characterization and optical properties of poly(aryleneethynylene)s Containing BODIPY

Abstract

Poly(aryleneethynylene)s containing BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) (P1) were prepared by palladium-catalyzed Sonogashira polymerization of 2,6-diiodo-functionalized BODIPY monomer (M1) with 1,4-diethynyl-2,5-didodecyl-oxybenzene monomer (M2). The structures of the monomer (M1) and copolymer (P1) were confirmed by 1 H-NMR and Fourier transform infrared (FTIR) spectroscopies; their optical properties were characterized by UV-Vis absorption, photoluminescence (PL) spectroscopy and the Z-scan technique. Both UV-Vis absorption and fluorescence emission of copolymer P1 red-shifted to longer wavelengths ( abs : from 502 nm to 542 nm;  em : from 511 nm to 631 nm) relative to those of the monomer M1 due to the π-conjugation extension of the copolymer. The third-order nonlinear optical coefficient ( (3) ) of copolymer P1 was 1.94 × 10 10 esu, which is almost two or three orders of magnitude greater than that of common conjugated polymers without BODPIY moiety.

Conjugated Polymers Containing BODIPY and Fluorene Units for Sensitive Detection of CN− Ions: Site-Selective Synthesis, Photo-Physical and Electrochemical Properties

“…4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivatives have been widely investigated in the fields of chemical sensors, solar cells, biological labeling, photodynamic therapy and nonlinear optical materials because of its unique advantages of high chemical and photo-stability, high extinction coefficients and fluorescence quantum yields, and narrow absorption and emission bands [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 ]. More interestingly, its optical properties could be effectively tuned by functionalizing BODIPY cores at the 2,6-, or 3,5-positions, or fusing some aromatic rings to the BODIPY core [ 1 , 2 , 3 , 4 , 5 , 12 ]. Incorporation of BODIPY dyes into the backbone of conjugated polymers is expected to integrate the unique properties of both BODIPY and conjugated polymers into one material for various potential applications, but the reports are limited [ 3 , 13 , 14 , 15 , 16 , 17 , 18 ].…”