BODIPY‐Based Porous Organic Polymers: How the Monomeric Methyl Substituents and Isomerization Affect the Porosity and Singlet Oxygen Generation

Abstract

Facile Friedel–Crafts coupling reaction prepared porous organic polymers BDP‐POP‐n (n = 1, 3, and 4) are reported. The influences of methyl substituents and single monomer isomerization on corresponding BDP‐POPs' porosity and singlet oxygen generation properties have been investigated. The obtained BDP‐POPs are thoroughly characterized by a combination of techniques such as Fourier transform infrared, solid 13C NMR, scanning electron microscopy, and transmission electron microscopy. In addition, these porous polymers' singlet oxygen generation capacities under visible green light (480–510 nm) irradiation are compared. Results show that BDP‐POP‐1, whose pyrrolyl ring bears methyl substituents and the two 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BDP) units are at para‐position of the phenyl ring, possesses the largest Brunauer–Emmett–Teller surface area and the best singlet oxygen generation ability. Control experiment reveals that the BDP‐POP‐1 shows superiority in generating singlet oxygen than that of model polymer CMPBDP. It is believed that this work may pave a road to design more effective porous materials for photocatalysis.

Architectures and Applications of BODIPY-Based Conjugated Polymers

“…Algi and coworkers [24] designed two BODIPY cores, bithiophene and EDOT, with three electroactive function groups, and the ensuing polymers 31 and 32 ( Figure 11) obtained via electrochemical polymerization possessed cellular structures and multi-electrochromic properties. Kuang and coworkers presented a series of BODIPY-based POPs 33-37 ( Figure 12) synthesized by Friedel-Crafts cross-coupling reactions to explore the influences of monomer structures on the porous properties and singlet-oxygen generation properties [65,66]. In comparison with analogs 33-34, 35, with a long space between two BODIPY units, showed higher surface area but worse photocatalytic activity of singlet-oxygen genera- Kuang and coworkers presented a series of BODIPY-based POPs 33-37 ( Figure 12) synthesized by Friedel-Crafts cross-coupling reactions to explore the influences of monomer structures on the porous properties and singlet-oxygen generation properties [65,66].…”

“…Kuang and coworkers presented a series of BODIPY-based POPs 33-37 ( Figure 12) synthesized by Friedel-Crafts cross-coupling reactions to explore the influences of monomer structures on the porous properties and singlet-oxygen generation properties [65,66]. In comparison with analogs 33-34, 35, with a long space between two BODIPY units, showed higher surface area but worse photocatalytic activity of singlet-oxygen genera- Kuang and coworkers presented a series of BODIPY-based POPs 33-37 ( Figure 12) synthesized by Friedel-Crafts cross-coupling reactions to explore the influences of monomer structures on the porous properties and singlet-oxygen generation properties [65,66]. In comparison with analogs 33-35, with a long space between two BODIPY units, showed higher surface area but worse photocatalytic activity of singlet-oxygen generation.…”

“…Kuang and coworkers presented a series of BODIPY-based POPs 33 – 37 ( Figure 12 ) synthesized by Friedel-Crafts cross-coupling reactions to explore the influences of monomer structures on the porous properties and singlet-oxygen generation properties [ 65 , 66 ]. In comparison with analogs 33 – 35 , with a long space between two BODIPY units, showed higher surface area but worse photocatalytic activity of singlet-oxygen generation.…”

BODIPY‐based Carbonaceous Materials for High Performance Electrical Capacitive Energy Storage

“…[24] Few works were launched using BODIPY units to prepare porous organic polymers (POPs) and the application of this kind POPs were restricted to heterogeneous photocatalysis. [25][26][27][28] To carry forward this kind POPs, our group showedt he BODIPY core can adsorb volatile iodine through ac hemical adsorption mechanism and the capacity reachedt o2 830 mg g À1 . [29] Very recently,J iang and co-workers designed and developed as eries of BODIPY containing POPs delivering enhanced affinities with CO 2 due to the existence of boron,n itrogen and fluorine.…”

“…On the other hand, 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) related compounds are hot research topics due to their excellent photophysical properties and potential applications in functional materials . Few works were launched using BODIPY units to prepare porous organic polymers (POPs) and the application of this kind POPs were restricted to heterogeneous photocatalysis . To carry forward this kind POPs, our group showed the BODIPY core can adsorb volatile iodine through a chemical adsorption mechanism and the capacity reached to 2830 mg g −1 .…”