Abstract
FeCl3-mediated oxidative cyclization was successfully used to construct an extended thiophene-pendant pyrene skeleton and synthesize a novel thiophene-fused polycyclic aromatic (THTP-C) with a tetracene core. The identity of the compound was confirmed by 1H-NMR, 13C-NMR, MS, and elemental analysis. Meanwhile, a single crystal of THTP-C was obtained and analyzed by X-ray single-crystal diffraction. THTP-C has a “saddle” shaped π-conjugated 1-D supramolecular structure, and favors highly ordered self-assembly by π-π interactions as evidenced by its concentration-dependent 1H-NMR spectra in solution. The optical properties of THTP-C were investigated by ultraviolet-visible (UV-Vis) and photoluminescence (PL) spectroscopy and its electrochemical properties were investigated by cyclic voltammetry (CV). The relatively large band gap (2.86 eV), low EHOMO level (−5.64 eV) and intermolecular π-π interactions imply that THTP-C has a high stability against photo-degradation and oxidation, and may be a promising candidate for stable hole-transporting materials.
Highlights
Organic semiconductors based on π-conjugated aromatics have been well-investigated due to their potential applications as active organic semiconductor layers in a variety of organic electronic devices.Acene and oligothiophene derivatives with high charge-carrier mobility in the solid state represent two of the most heavily studied series of compounds and are used as organic semiconductor materials in organic light emitting diodes (OLEDs), solar cells and organic field effect transistors (OFETs) [1,2].Many efforts have been devoted to the synthesis and applications in organic-based electronic devices of various π-conjugated homoaromatic and heteroaromatic systems, and oligomers and polymers derived from acene and thiophene derivatives
We have reported the successful synthesis of two new thiophene-containing oligomers based on a pyrene core with pendant thienyl rings [11]; an expanded and elongated conjugated system would be expected to lead to even more interesting electronic and optical properties
THTP-C with a larger rigid tetracene core, while it could not be successfully applied to electron-rich precursor 4,5,9,10-tetra(2-thienyl)-2,7-di-tert-butylpyrene (TTP)
Summary
Organic semiconductors based on π-conjugated aromatics have been well-investigated due to their potential applications as active organic semiconductor layers in a variety of organic electronic devices. Many efforts have been devoted to the synthesis and applications in organic-based electronic devices of various π-conjugated homoaromatic and heteroaromatic systems, and oligomers and polymers derived from acene and thiophene derivatives. Heteroaromatic oligomers derived from acene and thiophene have received considerable attention due to their unique photophysical properties and the feasibility of chemical modification, as well as their good stability against photo-degradation and oxidation. We have reported the successful synthesis of two new thiophene-containing oligomers based on a pyrene core with pendant thienyl rings [11]; an expanded and elongated conjugated system would be expected to lead to even more interesting electronic and optical properties. To assess its intrinsic potential as an opto-electronic and organic semiconductor material, the photophysical properties of THTP-C were studied using UV-Vis absorption and PL spectroscopy both in solution and thin film. Single-crystal crystallographic analysis was applied to elucidate the crystal structure of THTP-C
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