一类含吡咯和吩噻嗪环的n型有机半导体的设计、合成和性质

PBBTZ (6H-吡咯[3,2-b:4,5-b´]双[1,4]苯并吩噻嗪) 是我们刚刚报道的一类高场效应性能p型有机半导体材料。本文用简单的一锅合成法制备了两种三氟甲基取代的 PBBTZ衍生物3a和3b, 用1H NMR, IR, HRMS (EI-TOF), 元素分析等手段进行了表征，并描述和讨论了3b的晶体结构。用UV-Vis 和荧光光谱法研究了它们的光学性质，用循环伏安法研究了电化学性质，用热重分析法研究了热力学性质。研究表明，3a和3b的能隙由光谱最大吸收峰起峰位置估算分别为 2.45和2.48 eV, 溶液具有绿色荧光。3a的LUMO 和HOMO能级分别为-5.73和-3.28 eV，3b的LUMO 和HOMO能级分别为-5.67和-3.19 eV，均比PBBTZ有所下降。低能级使它们具有良好的空气稳定性，并且可能作为有前途的n型有机半导体材料应用于有机电子器件。

Synthesis and Properties of Heteroacenes Containing Pyrrole and Thiazine Rings as Promising n‐Type Organic Semiconductor Candidates

PBBTZ (6H‐pyrrolo[3,2‐b:4,5‐b′]bis[1,4]benzothiazine) was a p‐type semiconductor with high field‐effect transistor (FET) performance that we have just reported. Two trifluoromethyl substituted PBBTZ derivatives 3a and 3b were synthesized from facile one‐pot condensation. They were characterized by means of ¹H NMR, IR, HRMS (EI‐TOF) and elemental analysis, furthermore, the crystal structure of 3b was described and discussed. Their optical properties were studied by UV‐Vis and fluorescence spectroscopy, electrochemical properties were investigated by cyclic voltammetry (CV), and thermal properties were evaluated by thermal gravimetric analysis (TGA). The energy gaps of 3a and 3b , taken directly from spectroscopic measurements, are as broad as 2.45 and 2.48 eV, leading to bluish green and green photoluminescence. The LUMO and HOMO energy levels are ?5.73 and ?3.28 eV for 3a , ?5.67 and ?3.19 eV for 3b , respectively. The low energy levels render them well air‐stable, and to be promising n‐type semiconductor candidates for use in organic electronics.