Synthesis and properties of fully conjugated macrocycles composed of m-diethynylene-phenylene-bridged two dibenzofuran, dibenzothiophene and carbazole units

Fully conjugated macrocycles la-lc composed of m-diethynylene-phenylene-bridged two dibenzofuran, dibenzothiophene and carbazole units were synthesized via Sonogashira cross coupling reactions under high-diluted condition. These conjugated macrocycles were fully characterized by H-1 NMR, C-13 NMR, FTIR, Mass spectroscopies and elemental analysis. Photophysical and redox properties of la-lc were investigated by means of UV-vis/fluorescence spectroscopies and cyclic voltammetry, respectively, and those features were compared with those of the corresponding linear phenylethynyldibenzoheterols 11a-11c. Furthermore, their structural and electronic insights were studied by theoretical calculations at the B3LYP/cc-pVDZ//B3LYP/6-31G(d) level of theory. (C) 2018 Elsevier Ltd. All rights reserved.