Bis(2-oxo-7-azaindolin-3-ylidene)benzodifuran-dione-based donor–acceptor polymers for high-performance n-type field-effect transistors

Abstract

Two donor–acceptor (D–A) conjugated polymers were synthesized using a strongly electron-deficient unit as the acceptor, and dithiophene and (E)-2-(2-(thiophen-2-yl)vinyl)thiophene as the donor units.

Recent Progress in High‐Mobility Organic Transistors: A Reality Check

“…By using the same azaBDO monomer and copolymerizing it with an alkylated bithiophene ( P42 ) and TVT comonomers, Zhang et al were able to continue with and further expanded this concept (note: P42 – P44 are not shown in Figure due to their close similarities to the other BDO polymers that we have shown in Figure ), reporting electron mobilities of up to 1.86 cm 2 V −1 s −1 * . A similar fluorination strategy to Lei et al was reported by Zheng et al Here they used a tetra‐fluorinated BDO monomer ( P43 ), suggesting that the fluorination might have a double function as a conformational lock.…”

Aza-Based Donor-Acceptor Conjugated Polymer Nanoparticles for Near-Infrared Modulated Photothermal Conversion

“…And a diblock copolymer mPEG-b-PHEP reported previously (Sun et al, 2014). bis(6-bromo-1-(4-decyltetradecyl)-2-oxo-7-azaindolin-3-ylidene)benzo[1,2-b:4,5-b′]-difuran-2,6(3H,7H)-dione (2Br-BABDF), (3,3′-didodecyl-[2,2′-bithiophene]-5,5′-diyl)bis(trimethylstannane) (2tin-BT), ((4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)-6-(trimethylstannyl)benzo[1,2-b:4,5-b']dithiophen-2-yl)dimethylstannyl)methylium (2tin-BDTT), and (E)-1,2-bis(3-dodecyl-5-(trimethylstannyl)thiophen-2-yl)ethene (2tin-TVT) were synthesized according to the methods that reported in documents (Li et al, 2016b; Zhang et al, 2017a). Tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 ), tri(o-tolyl)phosphine (P(o-tol) 3 ), and other chemicals were purchased from Sigma-Aldrich Chemical Company, Alfa Aeasar Chemical Company, and Sinopharm Chemical Reagent Co. Ltd., China.…”

“…Herein, we currently introduce another isoindigo derivative (BABDF) by replacing the outer benzene rings of BIBDF with aza rings (Figure 1), an obvious next step, synthesize three BABDF-based conjugated polymers (PBABDF-BDTT, PBABDF-BT, and PBABDF-TVT) and study their photothermal properties. On the one hand, the introduction of electronegative N atom could further enhance the electron-withdrawing power of acceptor which result in strong push-pull interaction and significant red-shifts of absorption (Zhang et al, 2017a). On the other hand, the N-substitution on backbone can produce non-covalent interaction (S…N and CH….N) and endows the polymer with improved planar structure, which can also lead the redshift of absorption (Jackson et al, 2013; Zhang et al, 2019).…”

Tunable charge-transport polarity in thienothiophene–bisoxoindolinylidene-benzodifurandione copolymers for high-performance field-effect transistors

“…16 This high electron affinity unit was then used to construct other ambipolar and n-type polymers with a maximum electron mobility exceeding 7 cm 2 V À1 s À1 . [17][18][19] We introduced methyl and methoxy groups to modify the structures (hereafter referred to as DMTT for dimethylthienothiophene and MOTT for dimethoxythienothiophene). Methyl substituents can tune the electronic and morphological effects in optoelectronics, [20][21][22] whereas methoxy substituents are used to typically form noncovalent SÁ Á ÁO interactions for highperformance p-type semiconductors.…”