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

doi:10.7503/cjcu20170099

Abstract

Abstract:

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.

Key words: Annulated-indigo, Acceptor, Synthesis, Property

CLC Number:

O626.32

TrendMD:

REN Baoyi, HUANG Dan, XU Qin, SUN Yaguang. Synthesis and Properties of a New Compound Derived from Annulated-indigo^†[J]. Chem. J. Chinese Universities, 2017, 38(9): 1584.

Figures/Tables 6

Scheme 1 Synthetic route of MT-BAI-TM

Fig.1 Absorption spectra of MT-BAI-TM in chlo-roform with concentration of 1.5×106 mol/L

Fig.2 Cyclic voltammogram curve of MT-BAI-TM

Fig.3 Optimized ground-state geometry of MT-BAI-TM

Fig.4 Calculated spatial distributions of HOMO(A) and LUMO(B) levels of MT-BAI-TM

Fig.5 GIWAX diffractogram(A) and in-plane(a)/out-of-plane(b) line-cut profiles(B) of sample S-1

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