新型环合靛蓝衍生物的合成及性质

Synthesis and Properties of a New Compound Derived from Annulated-indigo

设计合成了基于环合靛蓝单元的Donor-Acceptor(D-A)型小分子——2,2'-(-(((2,9-双(5-(2-癸基十四烷基)噻吩-2-基)-6,13-二氧代-6,13-二氢二吲哚[3,2,1de:3',2',1'-ij][1,5]萘啶-7,14-二基)双(噻吩-5,2-二基))双(甲基叉))双(3-氧-2,3-二氢-1H-茚-2,1-二叉))二丙二腈(MT-BAI-TM).采用密度泛函(DFT)理论计算了该化合物的前线分子轨道分布.利用紫外-可见吸收光谱和循环伏安法分析了化合物的能级和带隙特征;通过掠入射宽角X射线散射实验(GIWAXS)测试了旋涂薄膜样品S-1内MT-BAI-TM分子的堆积取向.MT-BAT-TM的深吸收、高电子亲和势及面向上(Face-on)堆积特征表明,其具有受体型有机半导体材料的性质.

In this paper,a donor-acceptor-type molecule,2,2＇-（-（（（ 2,9-bis（ 5-（ 2-decyltetradecyl） thiophen-2-yl）-6,13-dioxo-6,13-dihydrodiindolo[3,2,1-de： 3＇,2＇,1＇-ij][1,5]naphthyridine-7,14-diyl） bis（ thiophene-5,2-diyl）） bis（ methaneylylidene）） bis（ 3-oxo-2,3-dihydro-1H-indene-2,1-diylidene）） dimalononitrile（ MT-BAI-TM） was synthesized using the strategy of bay-annulation. The compound possessed deep absorption spectra extending to 820 nm and low-lying LUMO level of-3. 98 eV. The distribution of frontier molecular orbits was calculated by density functional theory（ DFT）. A face-on orientation between MT-BAI-TM molecules in spin-coating film（ sample S-1） was observed by grazing incidence wide angle X-ray scattering（ GIWAXS）.The characteristics of deep absorption,high electron affinity and face-on orientation of the compound indicate the nature of acceptor-type organic semiconductor. Hence,the MT-BAI-TM is an attractive candidate as acceptor materials for potential application in organic photovoltaic devices.