Rapid Synthesis of Thiophene‐Based, Organic Dyes for Dye‐Sensitized Solar Cells (DSSCs) by a One‐Pot, Four‐Component Coupling Approach

Abstract

This one-pot, four-component coupling approach (Suzuki-Miyaura coupling/C-H direct arylation/Knoevenagel condensation) was developed for the rapid synthesis of thiophene-based organic dyes for dye-sensitized solar cells (DSSCs). Seven thiophene-based, organic dyes of various donor structures with/without the use of a 3,4-ethylenedioxythiophene (EDOT) moiety were successfully synthesized in good yields based on a readily available thiophene boronic acid pinacol ester scaffold (one-pot, 3-step, 35-61%). Evaluation of the photovoltaic properties of the solar cells that were prepared using the synthesized dyes revealed that the introduction of an EDOT structure beside a cyanoacrylic acid moiety improved the short-circuit current (Jsc) while decreasing the fill factor (FF). The donor structure significantly influenced the open-circuit voltage (Voc), the FF, and the power conversion efficiency (PCE). The use of a n-hexyloxyphenyl amine donor, and our originally developed, rigid, and nonplanar donor, both promoted good cell performance (η=5.2-5.6%).

Crystal Structure of (4-Fluorophenyl)(2-(methylthio)thiophen-3-yl)methanone

“…[1][2][3] Moreover, polymeric thiophenes are also broadly utilized as thin-film transistors, organic field-effect transistors, organic light-emitting transistors (OLET), chemical sensors, and solar cells. [4][5][6][7] In view of the above mentioned importance, the synthesis and crystal structure of the title compound (4-fluorophenyl)(2-(methylthio)thiophen-3-yl)methanone is reported here.…”

Efficient charge collection of photoanodes and light absorption of photosensitizers: A review

“…Matsumura et al fabricated DSSC using thiophene based organic dyes. Nearly seven thiophene derivative dyes were synthesized and obtained PCE's in the range of 5.2% to 5.6% 128 . Anthracene bridged carbazoles (ML4 and ML5) were used both as sensitizers and cosensitizers in DSSC by Mallam et al This donor‐π‐conjugation‐acceptor sensitizers alone have reduced efficiency, but using them as cosensitizers with N719 enhances efficiency to 5.74% and 6.10%, that is 10% higher 129 .…”

“…Nearly seven thiophene derivative dyes were synthesized and obtained PCE's in the range of 5.2% to 5.6%. 128 Anthracene bridged carbazoles (ML4 and ML5) were used both as sensitizers and cosensitizers in DSSC by Mallam et al This donor-π-conjugation-acceptor sensitizers alone have reduced efficiency, but using them as cosensitizers with N719 enhances efficiency to 5.74% and 6.10%, that is 10% higher. 129 Hosseinnezhad et al studied two new indigo derivatives as photosensitizers in which indoxyl group act as electron donor and acrylic and cyanoacrylic acids as electron acceptors.…”

Successive Pd‐Catalyzed Decarboxylative Cross‐Couplings for the Modular Synthesis of Non‐Symmetric Di‐Aryl‐Substituted Thiophenes

“…Existing synthetic approaches for non-symmetric oligiothiophenes involve a combination of Stille couplings, [13,[39][40][41][42] Kumada-Corriu type couplings, [43][44][45] Suzuki-Miyura couplings, [32,39,40,42,[46][47][48] and/or C-H arylations [44,47,[49][50][51][52][53] (selected examples of previous work are highlighted in Figure 1). Among these, C-H arylation is the most atom-economic process and avoids the stoichiometric generation of heavy waste, but the reaction can require additional substrate functionalization to Figure 1.…”