Chlorination as a useful method to modulate conjugated polymers: balanced and ambient-stable ambipolar high-performance field-effect transistors and inverters based on chlorinated isoindigo polymers

Lei, Ting; Dou, Jin-Hu; Ma, Zhijun; Liu, Chenjiang; Wang, Jieyu; Pei, Jian

doi:10.1039/c3sc50245g

Cited by 116 publications

(105 citation statements)

References 44 publications

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“…2a). The electrophilic chlorination of isoindigo with N-chlorosuccinimide (NCS) has been previously reported for the synthesis of polymeric materials, 67 but until now has not been exploited in a molecular framework (Fig. 2b).…”

Section: Materials Synthesismentioning

confidence: 99%

The structural evolution of an isoindigo-based non-fullerene acceptor for use in organic photovoltaics

et al. 2015

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The structural evolution of a functional isoindigo-based non-fullerene acceptor led to the development of three new materials to address the deficiencies of the original framework. Owing to the versatility of the structure and the flexibility of the synthetic procedures, these three new materials were accessible from previously optimized reaction conditions and similar precursor materials. The influence of structural modification on the optical, electrochemical and thermal properties were assessed and correlated with DFT calculations to provide compelling evidence for the effect of each substitution and how they relate to each particular adaptation. The structure-property relationships were investigated for their photovoltaic performance in solution processable BHJ devices fabricated in inverted architectures. Evaluation of device performance demonstrated that a single modification did not improve on the efficiency of the original structure, but the combination of both induced nonplanarity, and increased electron affinity of the fourth iteration showed the potential of our framework, with PCE reaching 1.9%.

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Section: Materials Synthesismentioning

confidence: 99%

The structural evolution of an isoindigo-based non-fullerene acceptor for use in organic photovoltaics

et al. 2015

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“…随后, 该课题组又开发了一类新型的氯代异靛衍生物, 通过与联二硒给体共聚, 成功合成了氯代异靛基共聚物 PCII2Se [95] , 其最高空穴和电子迁移率分别为 . 2013 年, 张德清课题组 [96] 首次将 Pechmann 染料应用 OFETs 领域中, 设计并合成一类高迁移率的聚合物半导体材料 P-BPDTT, 其 HOMO/LUMO 能级分别为-5.0 和-3.7 eV, 利于空穴和电子的同时注入.…”

Section: 双极性聚合物半导体材料最新进展unclassified

Recent Advances in High-Mobility Polymeric Semiconductor Materials

Chen¹

2016

Chin. J. Org. Chem.

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Significant progress has been made in polymeric semiconductors and their organic field-effect transistors (OFETs) since 1980s. To date, hundreds of polymeric semiconductors have been reported and used for OFETs. The hole mobility above 36.3 cm 2 •V -1 •s -1 has been achieved, which can be competitive with organic small semiconductors and even amorphous silicon. In this review, the recent progress in high-mobility polymeric semiconductor materials has been summarized from the perspective of design, synthesis, and OFET devices performance. Moreover, the recent developments are systematically summarized and analyzed according to different types of polymeric semiconductors, including p-type, n-type, and ambipolar polymeric semiconductors. The analysis about the relationship among the molecular structure-aggregation structure-OFET devices performance may guide the rational molecule design in the polymeric semiconductor materials with excellently comprehensive performance in the future.

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“…To our surprise, compared with the TII monomer, the polymers did not show any obvious bathochromic-shifted absorption, which was not in accordance with the literature about the conjugated polymers of isoindigo. 7,13,21,22 Reynolds and coworkers have reported two low-energy gap oligothiophenes connected with isoindigo, both of which showed a greater red shift in the UV spectra. 6 To rule out the possible problems that might be involved in Stille coupling, a model compound cTII-2T, with two thiophene rings capped at either end of TII, was synthesized in the same way and well characterized (see the Experimental section for details).…”

Section: Methodsmentioning

confidence: 99%

Thiophene-fused isoindigo based conjugated polymers for ambipolar organic field-effect transistors

Zhao

Cai

et al. 2016

Polym. Chem.

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A series of donor-acceptor (D-A) type conjugated polymers based on novel thiophene-fused isoindigo (TII) were designed and synthesized via palladium catalyzed Stille copolymerization. We found that the redesign of the synthesis of brominated TII was necessary, and the α-bromination had to be completed at the very beginning, or β-brominated TII was obtained, which only led to cross conjugated polymers.Once the bromination was introduced at the correct position, fully conjugated D-A type polymers could be obtained. A series of fully conjugated polymers were obtained by Stille coupling polymerization of α-brominated TII with different donors, and among them, copolymers with thiophene (T) and (E)-1,2-bis (3-octylthiophen-2-yl)ethene (TVT-8) showed acceptable solubility and were suitable to fabricate solution-processable organic field-effect transistors (OFETs). Top-gate/bottom-contact (TG/BC) devices were constructed for the polymers to test their OFET performances. Both fully conjugated polymers exhibit two-orders of magnitude higher charge carrier mobilities than the cross conjugated ones, and PTII-T shows balanced electron and hole mobilities and PTII-TVT-8 is a p-type dominated semiconductor. These observations indicated that the developed TII unit that has improved coplanarity can be a promising building block for the construction of highly efficient conjugated polymers for OFET applications.

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Chlorination as a useful method to modulate conjugated polymers: balanced and ambient-stable ambipolar high-performance field-effect transistors and inverters based on chlorinated isoindigo polymers

Cited by 116 publications

References 44 publications

The structural evolution of an isoindigo-based non-fullerene acceptor for use in organic photovoltaics

The structural evolution of an isoindigo-based non-fullerene acceptor for use in organic photovoltaics

Recent Advances in High-Mobility Polymeric Semiconductor Materials

Thiophene-fused isoindigo based conjugated polymers for ambipolar organic field-effect transistors

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