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Paper | Regular issue | Vol 94, No. 6, 2017, pp.1040-1054
Published online, 8th May, 2017
DOI: 10.3987/COM-17-13685
Effect of End Groups on the Band Gap of Donor-Acceptor Based Small Molecules Containing Diketopyrrolopyrrole

Jin-Hee Han, Hun-Min Kang, Dong Jin Song, Baji Shaik, Yu Mi Heo, Hye Jin Chung, and Seung-Mann Paek*

*Department of Chemistry, College of Pharmacy and Research Institute of Pharmaceutical Sciences, Gyeongsang National University, Jinju daero, Jinju, Gyeongnam 660-701, Korea


(Acceptor-donor-acceptor type compounds 5,5'-(4,4'-(2,5-bis(2-octyldodecyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(4,1-phenylene))dithiophene-2-carbonitrile (DPPTCN), 4',4''-(2,5-bis(2-octyldodecyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)dibiphenyl-4-carbonitrile(DPPPhCN), 2,2'-(5,5'-(4,4'-(2,5-bis(2-octyldodecyl)-3,6-dioxo-2,3,5,6-tetra-hydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(4,1-phenylene))bis(thiophene-5,2-diyl))-bis(methan-1-yl-1-ylidene)dimalononitrile (DPPT2CN), 2,2'-(4',4''-(2,5-bis(2-octyldodecyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(bi-phenyl-4',4-diyl))bis(methan-1-yl-1-ylidene)dimalononitrile (DPPPh2CN) were designed and synthesized. All the compounds have central diketopyrrolopyrrole as common acceptor unit, the donor groups differ either thiophene or phenyl group and the terminal end groups are differ either nitrile or dicyanovinylene groups. In order to study the relationship between chemical structure and properties, their optical, thermal and electrochemical properties were investigated. Thermal properties indicate that all the compounds have high thermal stability. Among them, DPPT2CN with thiophene groups as donor and dicyanovinylene as acceptor has shown lowest LUMO energy level of -3.77 eV and low HOMO-LUMO band gap of 1.86 eV.