Abstract
The thianthrene–arylene conjugated units have been designed and synthesized via Suzuki or Stille coupling reaction. The structures and properties of the synthesized compounds were characterized by HNMR, CNMR, MS, UV-Vis absorption spectroscopy, fluorescence spectroscopy as well as electrochemical measurements. The luminescent studies demonstrate that thianthrenes are good chromophores. Also the electrical properties of obtained films confirm the applicable potential of these novel aryl-based π-conjugated polymers for the development of various electrical and electrochemical solid-state devices.
Highlights
Molecular organic materials with conjugated π-electron systems have found widespread use due to their special optical and electronic properties
Compound 3, under the adapted Suzuki coupling conditions,11,12 was converted to the desired thianthrene derivatives 4-7 (Scheme 2a) in moderate yields
Differential pulse voltammetry (DPV) spectra (Figure 2) exibit that oxidation potential peaks are similar for all thianthrene derivatives
Summary
Molecular organic materials with conjugated π-electron systems have found widespread use due to their special optical and electronic properties. Compound 3, under the adapted Suzuki coupling conditions,11,12 was converted to the desired thianthrene derivatives 4-7 (Scheme 2a) in moderate yields (around 50%). Whereas synthesis of compounds 9-13 was based on Stille coupling13 between different arylene-derivatives and dibromothianthrene [8] (Scheme 2b). The cross-coupling reaction of thianthren-1-yl boronic acid with dibromoalkyl derivatives of fluorene-, carbazole-, diphenylamine-, phenothiazine in the presence of catalytic amounts of Pd(PPh3)4 in a two-phases system (toluene/2M K2CO3 in volume ratio 2:1) at 90oC gave 4-7 in around 50% isolated yields, respectively.
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