Synthesis and opto‐electronic properties of functionalized pyrimidine‐based conjugated polymers

Abstract

Side chain engineering has been used for tuning the opto‐electronic properties of organic semiconductors. In this work, a series of pyrimidine‐based donor‐acceptor (D‐A) conjugated polymers functionalized with electron‐withdrawing or electron‐donating side chains were synthesized. The opto‐electronic properties of the pyrimidine D‐A conjugated polymers were investigated focusing on the dependence on the electron withdrawing strength of the acceptor moiety, while maintaining the same donor moiety. Fine‐tuning of the energy levels was achieved by introducing electron donating (alkoxy [OR] and alkylthio [SR]) or electron withdrawing (alkylsulfinyl [SOR] and alkylsulfonyl [SO2R]) side chains onto the acceptor moiety. The effects of side chain modification have been investigated through DFT calculations, UV–vis analysis, and electrochemical measurements. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 2547–2553

Chalcogenopheno[3,2-b]pyrrole-Containing Donor–Acceptor–Donor Organic Semiconducting Small Molecules for Organic Field-Effect Transistors

“…The chemical structures of all intermediates and targeted molecules were characterized by 1 H NMR, 13 C NMR, and DEPT 135 analyses. The molecular weights of ThDPP-TT, ThDPP-FP, ThDPP-TP, and ThDPP-SeP were determined by MALDI-TOF MS analysis (Figures S1−S70).…”

Siloxane Side-Chain-Modified Diketopyrrolopyrrole and Thienopyrrole Containing Small Molecules for Organic Field-Effect Transistors

“…Organic semiconducting materials (OSMs) gained attention within the last few decades due to their relatively low cost, light weight, flexibility, and tunable optoelectronic properties. − OSMs are used in organic field-effect transistors (OFETs), light-emitting diodes, solar cells, photodetectors, memory devices, chemical sensors, logic circuits, etc . Among organic electronic devices, OFETs are essential components in analog and digital integrated circuits. − OSMs are categorized into two types depending on their molecular backbone structure and molecular weight: small organic semiconducting molecules and semiconducting polymers.…”

“…25,28 Siloxane side chains also provide additional ambient stability to thin films, which offer an opportunity for processing in ambient conditions. 33 Our group reported TP-based semiconducting materials with reasonable hole mobilities for small molecules 22 [1,2,5]thiadiazole (BT)-and TP-based small molecules with different spacer units were reported with hole mobilities in the range of 10 −1 −10 −3 cm 2 V −1 s −1 . 5,21,22,34 Moreover, a diketopyrrolo [3,4-c]pyrrole (DPP)−TP-based copolymer was also reported with a hole mobility of over 10 −1 cm 2 V −1 s −1 .…”

Incorporation of Selenopheno[3,2-b]pyrrole into Benzothiadiazole-Based Small Molecules for Organic Field-Effect Transistors

“…Organic semiconductors are conjugated molecules that possess the electronic properties required for organic field-effect transistors (OFETs) applications. OFETs have proven to be promising in modern technology owing to their attractive features such as lightweight, low cost, flexibility, and solution processability. − Organic semiconductors can be classified into two groups: conjugated polymers and small organic conjugated molecules. Conjugated polymers have relatively high conjugation lengths favorable for charge carrier transfer, but batch-to-batch variation in molecular weight and polydispersity curtail their applications. − Comparatively, small conjugated molecules have precise molecular weights and well-defined structures.…”

“…Synthesized acrylate derivative was subjected to Hemetsberger cyclization in toluene to yield ethyl 2-bromo-4H-selenopheno[3,2b]pyrrole-5-carboxylate (5). It was further alkylated with 1bromododecane at the pyrrole-nitrogen atom to obtain the corresponding alkylated donor block (6). Synthesis of (V) and (VI) was accomplished by following similar procedures in the literature.…”