Development of Pyrene Derivatives as Promising n‐Type Semiconductors: Synthesis, Structural and Spectral Properties. Issue 12 (8th November 2017)

• Record Type: Journal Article
• Authors: Liu, Minglun; Gong, Xiaojie; Zheng, Chaoyue; Gao, Deqing
• Is Part Of: Asian journal of organic chemistry. Volume 6:Issue 12(2017)
• Page Start: 1903
• Page End: 1913
• Publication Date: 2017-11-08
• Subjects: conjugation -- pyrenes -- semiconductors -- solvatochromism -- substituent effects; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201700441
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A series of promising candidates for n‐type semiconductors, which were based on a 1, 6‐, 1, 8‐ and mono‐substituted pyrene‐thiophene backbone with a cyano group and dicyanovinylene moieties, were synthesized. The compounds were characterized using NMR spectroscopy, elemental analysis, UV‐vis, photoluminescence (PL), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), cyclic voltametry (CV) and DFT calculations. The substituent effects on molecular properties were studied in detail. It was found that the dicyanovinylene substitution enhanced the coplanarity of the π‐conjugated systems as compared to cyano substitution. The LUMO energy level was located deeply, and one of them had LUMO of below −4.00 eV, indicating that they may be promising candidates for n‐type semiconductors. Abstract : Just my type : A series of pyrene derivatives were synthesized. In contrast with 1, 6‐position substitution, 1, 8‐position substitution had smaller dihedral angles and facilitated large conjugation and intermolecular stacking. The dicyanovinylene substitution strengthened the coplanarity and enhanced π‐conjugated systems. The lowest unoccupied molecular orbital (LUMO) energy level was located deeply and they may be promising candidates of n‐type semiconductors.