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Pechmann Dye‐Based Molecules Containing Fluorobenzene Moieties for Ambipolar Organic Semiconductors
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2018-02-28 , DOI: 10.1002/ajoc.201700669
Hewei Luo 1 , Xiaobiao Dong 2 , Zhengxu Cai 3 , Lizhen Wang 1 , Zitong Liu 2
Affiliation  

Two hybrid A2‐D‐A1‐D‐A2 (A=acceptor, D=donor) molecules, that is, (E)‐5,5′‐bis[5‐(4‐fluorophenyl)thiophen‐2‐yl]‐1,1′‐dioctyl‐[3,3′‐bipyrrolylidene]‐2,2′(1H,1′H)‐dione (FBBPD) and (E)‐1,1′‐dioctyl‐5,5′‐bis[5‐(3,4,5‐trifluorophenyl)thiophen‐2‐yl]‐[3,3′‐bipyrrolylidene]‐2,2′(1H,1′H)‐dione (TFBBPD), were synthesized and characterized. Each of these compounds contain the Pechmann dye derivative (E)‐[3,3′‐bipyrrolylidene]‐2,2′(1H,1′H)‐dione (BPD) as the electron‐accepting core, which is flanked by an electron‐donor moiety (i.e., thiophene) and other electron acceptors (i.e., 4‐fluorobenzene or 3,4,5‐trifluorobenzene). Organic field‐effect transistor (OFET) results of FBBPD show ambipolar properties with electron (μemax) and hole mobilities (μhmax) up to 0.20 and 0.023 cm2 V−1 s−1, respectively. In comparison, the electron and hole mobilities of the OFET based on TFBBPD, which contains a more electron‐accepting moiety, are higher (μemax=0.58 cm2 V−1 s−1 and μhmax=0.054 cm2 V−1 s−1). X‐ray diffraction and atomic force microscopy studies were carried out to investigate the variations in the mobilities. Overall, these studies show the potential of BPD in hybrid D‐A molecules to act as the electron‐acceptor moiety in organic semiconducting studies.

中文翻译:

用于双极性有机半导体的含氟苯部分的基于Pechmann染料的分子

两个杂合的A 2 ‐D‐A 1 ‐D‐A 2(A =受体,D =供体)分子,即(E)‐5,5′‐双[5‐(4‐氟苯基)噻吩‐2‐基] -1,1'-二辛基[3,3'- bipyrrolylidene] -2,2'(1 ħ,1' ħ) -二酮(FBBPD)和(Ë)-1,1'-二辛基- 5, 5'-双[5-(3,4,5-三氟苯基)噻吩-2-基] - [3,3'- bipyrrolylidene] -2,2'(1 ħ,1' ħ) -二酮(TFBBPD),合成并表征。这些化合物的每含有Pechmann染料衍生物(ë) - [3,3'- bipyrrolylidene] -2,2'(1 ħ,1' ħ) -二酮(BPD)作为电子接受核,其侧翼是电子给体部分(即噻吩)和其他电子受体(即4-氟苯或3,4,5-三氟苯)。的有机场效应晶体管(OFET)结果FBBPD示出了具有电子双极特性(μ Ë最大值)和空穴迁移率(μ ħ最大值)至多0.20和0.023厘米2  V -1 小号-1,分别。相比较而言,基于该OFET的电子和空穴迁移率TFBBPD,它包含一个以上的电子接受部分,是更高(μ Ê最大=0.58厘米2  V -1 š -1μ ħ最大=0.054厘米2  V -1 小号-1)。进行了X射线衍射和原子力显微镜研究,以研究迁移率的变化。总体而言,这些研究表明,在有机半导体研究中,混合D-A分子中BPD可能充当电子受体部分。
更新日期:2018-02-28
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