Carbonyl-Functionalized Cyclazines as Colorants and Air-Stable n-Type Semiconductors

• DOI: 10.1021/acs.orglett.8b00183
• Publication Date: 2018-02-15T20:22:16Z
• Authors: Artem Skabeev; Ute Zschieschang; Yulian Zagranyarski; Hagen Klauk; Klaus Müllen; Chen Li
• Keywords: 01 natural sciences; 0104 chemical sciences

A series of π-extended cycl[3,3,2]azines (3) bearing additional carbonyl groups were synthesized via aldol condensations. Two strong electron acceptor molecules (4 and 5), with low-lying LUMO energy levels of -3.99 and -3.95 eV, respectively, were obtained. Organic thin-film transistors (TFTs) based on the cyanated cyclazine derivatives 5 were fabricated by vapor deposition, exhibiting extraordinarily stable n-type semiconductor character under ambient condition with the highest electron mobility of 0.06 cm2 V-1 s-1 consistently for more than 30 months.