Polyacetylenes containing BODIPY pendants with different connectivities: synthesis, characterization and opto-electronic properties

Liu, Bin; Li, Lingfeng; Lin, Cuiling; Zhou, Jingdan; Zhu, Zhexin; Xu, Hongyao; Qiu, Huayu; Yin, Shouchun

doi:10.1039/c3py01021j

Cited by 21 publications

(9 citation statements)

References 63 publications

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“…Additionally, BODIPYs can be incorporated into conjugated polymers as pendant side chains through meso- or α-positions. Yin and coworkers [ 55 ] synthesized three polyacetylenes 27 – 29 bearing BODIPYs as pendant side chains through meso- or α-positions ( Figure 9 ) and investigated the effect of connective methods on the properties of the obtained polymers. Polymers 28 and 29 displayed poorer thermal stability than 27 because the coplanarity of backbone and BODIPY units in polymers 28 and 29 reduced the thermal resistance of polymers.…”

Section: Structures Of Bodipy-based Conjugated Polymersmentioning

confidence: 99%

Architectures and Applications of BODIPY-Based Conjugated Polymers

et al. 2020

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Conjugated polymers generally contain conjugated backbone structures with benzene, heterocycle, double bond, or triple bond, so that they have properties similar to semiconductors and even conductors. Their energy band gap is very small and can be adjusted via chemical doping, allowing for excellent photoelectric properties. To obtain prominent conjugated materials, numerous well-designed polymer backbones have been reported, such as polyphenylenevinylene, polyphenylene acetylene, polycarbazole, and polyfluorene. 4,4′-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-based conjugated polymers have also been prepared owing to its conjugated structure and intriguing optical properties, including high absorption coefficients, excellent thermal/photochemical stability, and high quantum yield. Most importantly, the properties of BODIPYs can be easily tuned by chemical modification on the dipyrromethene core, which endows the conjugated polymers with multiple functionalities. In this paper, BODIPY-based conjugated polymers are reviewed, focusing on their structures and applications. The forms of BODIPY-based conjugated polymers include linear, coiled, and porous structures, and their structure–property relationship is explored. Also, typical applications in optoelectronic materials, sensors, gas/energy storage, biotherapy, and bioimaging are presented and discussed in detail. Finally, the review provides an insight into the challenges in the development of BODIPY-based conjugated polymers.

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Section: Structures Of Bodipy-based Conjugated Polymersmentioning

confidence: 99%

Architectures and Applications of BODIPY-Based Conjugated Polymers

et al. 2020

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“…EOE-BODIPY showed the typical absorption and emission spectra of the BODIPY chromophore, that is, the strong S 0 →S 1 (π-π * ) transition at 502 nm, the weak S 0 →S 2 (π-π * ) transition at 350 nm, and bright (Φ f = ~1.0) and sharp emission at 511 nm. Following the Sonogashira reaction of polymerization, both the absorption and emission peaks of copolymer P1 exhibited a broadening of the peaks and significant red-shifts to 542 nm (absorption) and 631 nm (emission) relative to EOE-BODIPY, which is a consequence of the π-conjugated system being extended [17,20] . However, the absolute quantum yield (Φ f ) of the copolymer was a small fraction of the EOE-BODIPY quantum yield (decrease from ~1.0 to 0.04).…”

Section: Optical Propertiesmentioning

confidence: 98%

“…They found that the BODIPY component in the π-conjugated copolymers played decisive roles in the nonlinear optical properties of the material, and the third-order nonlinear optical coefficients of the copolymers were enhanced gradually with the increased incorporation of the BODIPY component. Similarly, we investigated the effect of the position number of the BODIPY core at which it is conjugated to polyacetylene backbones on the material's nonlinear optical properties [17] . We found that the BODIPY position at which the dye was joined with the polyacetylene backbones had a significant effect on the resulting nonlinear optical properties, with the position 3 variant possessing ~15 times greater third-order nonlinear optical coefficients than those with the position 8 variant.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2015

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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.

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“…Meso-aryl functionalized BODIPYs are highly desirable building blocks to synthesize simple BODIPY based systems [18][19][20][21][22] to complex light harvesting arrays, 23 photonic wires, 24 and opto-electronic gates. 25,26 The meso-aryl functionalized BODIPYs can be prepared easily by following the well-established Lindsey's 27 traditional Lewis acid catalyzed approach. In Lindsey's approach, the synthesis of meso-aryl functionalized BODIPYs involves the condensation reaction between α-free pyrrole and functionalized aryl aldehydes in the presence of a catalytic amount of Lewis acid to obtain dipyrromethane which is on subsequent oxidation by DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) to dipyrromethene followed by BF 2 complexation using BF 3 ⋅ OEt 2 under basic conditions to yield meso-aryl BODIPYs ( Figure 2).…”

Section: Meso-functionalized Bodipys Meso-aryl Functionalized Bodipysmentioning

confidence: 99%