Donor-pi-Acceptor Type Diphenylaminothiophenyl Anthracene-mediated Organic Photosensitizers for Dye-sensitized Solar Cells

Abstract

Two new metal-free organic dyes bridged by anthracene-mediated it-conjugated moieties were successfully synthesized for use in a dye-sensitized solar cell (DSSC). A N,N-diphenylthiophen-2-amine unit in these dyes acts as an electron donor, while a (E)-2-cyano-3-(thiophen-2-yl)acrylic acid group acts as an electron acceptor and an anchoring group to the TiO2 electrode. The photovoltaic properties of (E)-2-cyano-3-(5-((10-(5-(diphenylamino)thiophen-2-yl)anthracen-9-yl)ethynyl)thiophen-2-yl)acrylic acid (DPATAT) and (E)-2-cyano-3-(5'-((10-(5-(diphenylamino)thiophen-2-yl)anthracen-9-yl)ethynyl)-2,2'-bithiophen-5-yl)acrylic acid (DPATABT) were investigated to identify the effect of conjugation length between electron donor and acceptor on the DSSC performance. By introducing an anthracene moiety into the dye structure, together with a triple bond and thiophene moieties for fine-tuning of molecular configurations and for broadening the absorption spectra, the short-circuit photocurrent densities (J(sc)), and open-circuit photovoltages (V-oc) of DSSCs were improved. The improvement of J(sc) in DSSC made of DPATABT might be attributed to much broader absorption spectrum and higher molecular extinction coefficient (epsilon) in the visible wavelength range. The DPATABT-based DSSC showed the highest power conversion efficiency (PCE) of 3.34% (eta(max) = 3.70%) under AM 1.5 illumination (100 mW cm(-2)) in a photoactive area of 0.41 cm(2), with the J(sc) of 7.89 mA cm(-2), the V-oc of 0.59 V, and the fill factor (FF) of 72%. In brief, the solar cell performance with DPATABT was found to be better than that of DPATAT-based DSSC.