Influence of synthetic pathway, molecular weight and side chains on properties of indacenodithiophene-benzothiadiazole copolymers made by direct arylation polycondensation

Abstract

Atom-economic protocols for the synthesis of poly(indacenodithiophene-alt-benzothiadiazole) (PIDTBT) are presented in which all C-C coupling steps are achieved by direct arylation. Using two different synthetic pathways, PIDTBT copolymers with different...

Biodegradable Polyimidazole Particles as Contrast Agents Produced by Direct Arylation Polymerization

“…By contrast, direct C-H arylation offers a more atom economic alternative, especially to Suzuki-coupling. [17][18][19][20] The direct arylation approach has already been applied to the synthesis of conjugated polymers; 21 however, it has not yet been adapted to the dispersion polymerization protocol to synthesize narrowly dispersed or uniform conjugated polymer particles.…”

“…Alternatively, they can be transformed to theranostic nanoparticles by surface functionalization so that specific biomolecular targeting motifs can be attached, allowing site-specific staining for contrast as well as for drug release. , Dispersion polymerization is one means to obtain conjugated polymer nanoparticles of low dispersity. − This polymerization technique allows precise adjustment of the particle size in the range of about 100 nm and up to the micrometer scale under mild reaction conditions. − A variety of transition metal-based C–C cross-coupling reactions like Suzuki, Heck, and Sonogashira coupling have been employed in dispersion polymerization protocols, yielding uniform and monodisperse particles. − However, the monomers for these coupling reactions need to be equipped with specific functional groups to take part in the catalytic cycle. By contrast, direct C–H arylation offers a more atom economic alternative, especially to Suzuki coupling. − The direct arylation approach has already been applied to the synthesis of conjugated polymers; however, it has not yet been adapted to the dispersion polymerization protocol to synthesize narrowly dispersed or uniform conjugated polymer particles.…”

Temperature-dependent morphology-electron mobility correlations of naphthalene diimide-indacenodithiophene copolymers prepared via direct arylation polymerization

“…Compounds Ph6IDT, NDIBr2 and the model compound Ph8-PIDT were synthesized according to published protocols. 59,60,69 Detailed information about instrumentation and experimental procedures are described in the Electronic Supplementary Information (ESI †). SEC curves of the samples P1-P7 are shown in Figure S5.…”

“…A reduction of the reaction temperature may suppress degradation of NDI-Br chain ends, similar to previously reported IDT copolymers with benzodiathiazole. 60 Interestingly, all polymerizations stopped following gelation of the mixture after a few hours, indicating a rapid build-up of MW. An exception is entry P1, where the low concentration and higher catalyst Please do not adjust margins Please do not adjust margins loading in combination with the addition of a phosphine-ligand facilitates nucleophilic substitution of NDI-Br chain ends by pivalate, leading to NDI-OH end groups (after hydrolysis) and accordingly low molar mass.…”

“…28,[56][57][58] Recently, we reported synthesis of well-defined IDT homo-and copolymers via DAP. 59,60 However, in order to optimize the performance of the material it is essential to understand its structure-property relationships. The influence of MW, end groups, processing solvents and post-temperature treatments are important factors that govern morphology and need to be optimized to understand the performance of new materials for organic electronics.…”