Palladium-catalyzed Direct Arylation Approach to Synthesize Naphthalene Bisimide-based Low-band-gap Polymers

Nakabayashi, Kazuhiro; Mori, Hideharu

doi:10.1246/cl.130201

Cited by 36 publications

(29 citation statements)

References 20 publications

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“…13,18 Indeed, commonly used Stille polycondensation protocols entail environmental and safety issues, and the fewreported DAP protocols for the synthesis of NDI-based copolymers were either inefficient, led to low molecular weight (MW) or did not allow for structural versatility. 16,[19][20][21] Another intriguing feature of the recently established DAP protocol involves MW control through the in situ C-H activation of aromatic solvents, which clearly increases the degree of synthetic control and thus brings DAP to the forefront of synthetic methods also for this class of materials. 13,18 However, although aromatic solvents are best suited to overcome limited solubilities of conjugated polymers, to control MW and are less toxic than the often used dimethylacetamide (DMAc) in DAP, 7 they are neither ideal considering the principles of green chemistry.…”

Section: Introductionmentioning

confidence: 99%

Effects of PNDIT2 end groups on aggregation, thin film structure, alignment and electron transport in field-effect transistors

et al. 2016

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To develop greener protocols toward the sustainable production of conjugated polymers, we combine the advantages of atom-economic direct arylation polycondensation (DAP) with those of the green solvent 2-methyltetrahydrofuran (MeTHF). The n-type copolymer PNDIT2 is synthesized from unsubstituted bithiophene (T2) and 2,6-dibromonapthalene diimide (NDIBr 2 ) under simple DAP conditions in MeTHF.Extensive optimization is required to suppress nucleophilic substitution of NDIBr end groups, which severely limits molar mass. Different carboxylic acids, bases, palladium precursors and ligands are successfully screened to enable quantitative yield and satisfyingly high molar masses up to M n,SEC B 20 kDa. In contrast to PNDIT2 made via DAP in toluene with tolyl-chain termini, nucleophilic substitution of NDIBr chain ends in MeTHF finally leads to NDI-OH termination. The influence of different chain termini on the optical, thermal, structural and electronic properties of PNDIT2 is investigated. For samples with identical molecular weight, OH-termination leads to slightly reduced aggregation in solution and bulk crystallinity, a decreased degree of alignment in directionally deposited films, and a consequently reduced, but not compromised, electron mobility with promising values still close to 0.9 cm 2 V À1 s À1.

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Section: Introductionmentioning

confidence: 99%

Effects of PNDIT2 end groups on aggregation, thin film structure, alignment and electron transport in field-effect transistors

et al. 2016

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“…On the other hand, direct C-H arylation polymerization has attracted much attention because it presents an economically and ecologically attractive alternative to the traditional cross-coupling reactions. [26][27][28][29]38,39,[44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60][61] Recently, the application of directly arylated polymers to the preparation of OPVs has been investigated. 45,54,55 In this study, we report the synthesis and characterization of double acceptor copolymers, -(CPDT-TPD-CPDT-BT) n -, comprising TPD, BT and two CPDT units in the polymer-repeating unit (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Double acceptor donor–acceptor alternating conjugated polymers containing cyclopentadithiophene, benzothiadiazole and thienopyrroledione: toward subtractive color organic photovoltaics

Chang

Muto

Kondo

et al. 2016

Polym J

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Double acceptor copolymers comprising benzothiadiazole (BT), thieno [3,4-c]pyrrole-4,6-dione (TPD) and two cyclopentadithiophene (CPDT) units, and a series of copolymers comprising CPDT-A-CPDT (A: acceptor = BT or TPD) with different numbers of thiophene units have been synthesized by combinations of Suzuki and Stille coupling, direct arylation and oxidative polymerization. Ultraviolet-visible absorption spectra and cyclic voltammograms were measured to compare the optical and electrochemical properties of the polymers. The double acceptor copolymer exhibited hybridized features resulting from the presence of both BT, as well as TPD. On the other hand, an increase in the number of electron donor units resulted in an increase in the band gap for both the TPD and BT series. Organic photovoltaics (OPV) devices were fabricated using the polymers and a fullerene derivative. These donor-acceptor alternating copolymers showed higher OPV performance (power conversion efficiency = 3-4%) than other polymers. The active layer comprising the double acceptor polymer and a fullerene derivative showed subtractive color resulting from wide-range visible light absorption, which is advantageous for developing transparent building-integrated OPVs. The OPV performance of BT-based copolymers synthesized via direct arylation was comparable or lower compared with those prepared by conventional cross-coupling polymerizations.

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“…The brominated monomer 5 was used to prepare the copolymers by reacting with the non-activated thiophene derivatives 8, 9 and 7 via direct DAP to give Polymers P1-3, respectively. More synthetic details are 40 described in Experimental Section.…”

Section: Synthesis and Structural Characterizationmentioning

confidence: 99%

Direct arylation polycondensation for efficient synthesis of narrow-bandgap alternating D–A copolymers consisting of naphthalene diimide as an acceptor

Shao

Wang

et al. 2015

Polym. Chem.

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A series of narrow-bandgap polymers based on an alkylthiophene-flanked naphthalene diimide (TNDI) were synthesized through direct arylation polycondensation. The 1 H NMR spectra indicate all polymers correspond to an 10 alternating copolymer structure with good regioregularity. Their photophysical, electrochemical, thermal and charge transport properties are characterized. Among all of the synthesized polymers, the copolymer consisting of alternating TNDI and 4,6-di-(2-thienyl)thieno[3,4-c][1,2,5]thiadiazole 15 performs the best in the thin film transistors, with a moderate hole mobility of 4.6 × 10 -3 cm 2 V -1 s -1 under ambient condition.

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Palladium-catalyzed Direct Arylation Approach to Synthesize Naphthalene Bisimide-based Low-band-gap Polymers

Cited by 36 publications

References 20 publications

Effects of PNDIT2 end groups on aggregation, thin film structure, alignment and electron transport in field-effect transistors

Effects of PNDIT2 end groups on aggregation, thin film structure, alignment and electron transport in field-effect transistors

Double acceptor donor–acceptor alternating conjugated polymers containing cyclopentadithiophene, benzothiadiazole and thienopyrroledione: toward subtractive color organic photovoltaics

Direct arylation polycondensation for efficient synthesis of narrow-bandgap alternating D–A copolymers consisting of naphthalene diimide as an acceptor

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