薁乙炔封端的萘二酰亚胺小分子的设计合成与场效应性能研究
收稿日期: 2016-09-27
修回日期: 2016-10-25
网络出版日期: 2016-11-17
基金资助
国家自然科学基金（No.21522209）、战略性先导科技专项B类（No.XDB12010100）和上海市科委（No.16JC1400603）资助项目.
Naphthalene Diimides Endcapped with Ethynylazulene: Molecular Design, Synthesis and Properties
Received date: 2016-09-27
Revised date: 2016-10-25
Online published: 2016-11-17
Supported by
Project supported by the National Natural Science Foundation of China (No. 21522209), the "Strategic Priority Research Program" (No. XDB12010100) and the Shanghai Science and Technology Committee (No. 16JC1400603).
薁是一种青蓝色的具有较大分子偶极矩的化合物.与传统的芳香化合物不同，薁类化合物具有特殊的光电性质.分别以薁的2-位和6-位通过叁键与萘二酰亚胺相连接合成了两个同分异构体化合物1和2.鉴于薁七元环的缺电子性和五元环的富电子性，通过不同的连接位点，两个化合物在物理化学性质以及器件性能方面表现出显著差异.理论计算表明，6-乙炔基薁封端的萘二酰亚胺衍生物2具有更低的最低空轨道（LUMO）能级和更好的LUMO电子离域性.通过旋涂的方法制备了两个化合物1和2的有机场效应晶体管（OFET）器件，在氮气条件下测得1和2的电子迁移率分别为0.022和0.16 cm2·V-1·s-1，基于化合物2的OFET器件表现出更优的场效应性能，这和理论计算所得结果相一致.
辛涵申 , 葛从伍 , 傅丽娜 , 杨笑迪 , 高希珂 . 薁乙炔封端的萘二酰亚胺小分子的设计合成与场效应性能研究[J]. 有机化学, 2017 , 37(3) : 711 -719 . DOI: 10.6023/cjoc201609029
Azulene is noteworthy for its deep blue color with a large dipole moment. Compared to other unsaturated aromatic hydrocarbons, azulenes show unique photophysical and electrical properties. Herein, two isomers of 1,4,5,8-naphthalene diimide (NDI) endcapped with ethynylazulene units (1 and 2) are presented, which are capped with five-membered and seven-membered rings of azulene moieties, respectively. It is interesting that these two compounds show remarkably different physicochemical properties, thermal stabilities and organic field-effect transistors (OFET) performance resulting from the different connections of an electron-rich five-membered ring and an electron-poor seven-membered ring. Density functional theory (DFT) calculations reveal that the lowest unoccupied molecular orbital (LUMO) energy of 2 (endcapped with 6-ethynylalzulene) is lower than that of 1 (endcapped with 2-ethynylalzulene), and 2 makes the electrons of LUMO more delocalized, which favor the overlap of LUMO between molecules, thus to obtain higher mobility for 2. OFETs based on thin films of these two isomers were fabricated with conventional spin-coated techniques. Under nitrogen atmosphere, 1 and 2 show n-type semiconducting properties with electron mobilities of up to 0.022 and 0.16 cm2·V-1·s-1, respectively, which is consistent with the DFT results.
Key words： azulene; naphthalene diimide; isomer; organic field-effect transistors; mobility
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