Vinylidenedithiophenmethyleneoxindole: a centrosymmetric building block for donor–acceptor copolymers

Abstract

A novel building block (VDTOI) was designed and synthesized. VDTOI-based copolymers exhibit a high mobility of 0.35 cm2 V−1 s−1.

Dithienylmethanone‐Based Cross‐Conjugated Polymer Semiconductors: Synthesis, Characterization, and Application in Field‐Effect Transistors

“…All these mobility values are apparently higher than ones measured from their respective as‐spun thin films, implying that strong molecular self‐assemble behaviors occur in the thermal annealing processes . It is notable that PDMO‐S exhibited higher hole mobilities than those of PDMO‐Se , suggesting that the chalcogen elements, sulfur and selenium, induced intrinsically different molecular aggregations and electronic properties that could also be observed in other conjugated polymer materials . In addition, the highest mobility of PDMO‐S is apparently lower than 0.97 cm 2 V −1 s −1 of its linearly conjugated counterpart, DPP‐quaterthiophene copolymer, reported by Li et al We attributed this to that intrachain transport is partially hampered in the cross‐conjugated systems.…”

“…The onset oxidation potential ( ) is 1.17 V for PDMO‐S and 1.09 V for PDMO‐Se, versus Ag/AgCl. Thus, the highest occupied molecular orbital (HOMO) energy levels of PDMO‐S and PDMO‐Se were estimated to be −5.57 and −5.49 eV, respectively, calculated according to the equation E HOMO = – (4.4 + ) eV . Meanwhile, the onset reduction potentials ( ) is −0.82 V for PDMO‐S and −0.91 V for PDMO‐Se , based on which the lowest unoccupied molecular orbital (LUMO) energy levels of PDMO‐S and PDMO‐Se were estimated to be −3.58 and −3.49 eV, respectively, according to the equation E LUMO = – (4.4 + ) eV.…”

“…Nowadays, there are successful approaches adopted in developing high‐performance linear conjugated polymer for PFETs such as designing planar building blocks including electron‐donating and electron‐withdrawing building blocks, tuning polymeric conjugated backbone conformation through incorporating intramolecular interactions (conformational locks), increasing the order of molecular aggregation and solution‐processability by introducing functional side chains, and optimizing the frontier orbital energy levels by loading suitable heteroatom‐substituted groups on polymeric conjugated backbones . Depended on these approaches, we had developed two dione‐bridged cross‐conjugated alternating polymers, in which the dione‐bridging moiety is firstly adopted as π ‐extended building block in constructing organic semiconductors for PFETs .…”

Centrosymmetric Thiophenemethyleneoxindole‐Based Donor–Acceptor Copolymers for Organic Field‐Effect Transistors

“…S. Li reported polymers containing ITTI for organic photovoltaic cell applications that demonstrated a power conversion efficiency as high as 6.4% . Zhang et al introduced a similar monomer, (3Z,3′Z)‐3,3′‐((5,5′(E)‐ethene‐1,2‐diyl)bis(thiophene‐5,2‐diyl))‐bis(methany‐lylidene))bis(indolin‐2‐one) (ITETI; Figure S1, Supporting Information), into the D‐A polymer backbone and showed p‐type transport characteristics, with a highest mobility of 0.35 cm 2 V −1 s −1 . Compared to ITETI, 2‐(thiophen‐2‐yl)thiophene substituted for 2,(2‐(thiophen‐2‐yl)vinyl)thiophene will benefit the planarity of ITTI in the solid state.…”

Rational design of diarylethylene‐based polymeric semiconductors for high‐performance organic field‐effect transistors

“…DAE are a kind of π ‐extended vinyl‐bridged biaryl building blocks, in which the aryl groups could be the same, or different (Fig. ) . Some representative DAE units 1 − 15 are shown in Figure .…”