Synthesis and Photovoltaic Properties of Efficient Organic Dyes Containing the Benzo[b]furan Moiety for Solar Cells

Abstract

New organic dyes composed of the benzo[b]furan donor, thiophene-conjugated bridge, and cyano acrylic acid acceptor have been newly synthesized through the one-pot coupling cyclization key step. Nanocrystalline TiO2 dye-sensitized solar cell was fabricated using this dye. A solar-to-electric conversion efficiency of 6.65% and 4.70% is achieved with 1 and 2, respectively.

Mapping the frontier electronic structures of triphenylamine based organic dyes at TiO2interfaces

“…[4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] Specifically the organic sensitizers compete with the more traditional dyes in the thin solid solar cells where high extinction coefficients of the dyes are needed for efficient light harvesting. The relatively easy synthetic routes of organic dye makes them easy to modify with respect to position of the energy levels important for the DSC energy conversion.…”

Synthesis of Organic Dyes with Linkers Between 9,9-Dimethylfluorenyl Terminal and α-Cyanoacrylic Acid Anchor, Effect of the Linkers on UV-Vis Absorption Spectra, and Photovoltaic Properties in Dye-Sensitized Solar Cells

“…14 Suzuki coupling of 15 with iodide 8 (59%), hydrolysis of the acetal protecting group under aqueous acidic condition (97%), and finally condensation of the resulting aldehyde with cyanoacetic acid (52%) completed the synthesis of organic dye 3. 15 Organic dye 4 was prepared from 6-chloronicotinic acid (16) (Scheme 4). Transformation of 16 into the boronate 17 was (PPh3)2Cl2 (0.09 eq), 2-thiopheneboronic acid (9) (1.1 eq), 2 M Na2CO3-DME-H2O (5 : 9 : 1), reflux, overnight, 60%.…”

“…15 Synthesis of organic dye 5 was summarized in Scheme 5. Commercially available 2,2'-bithiophene (18) was transformed into the C-2 boronate ester (42%) by treatment of n-BuLi and quenching with 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (14), 14 and the boronate ester was subsequently coupled with iodide 8 to produce the bis-thiophene intermediate 19 in 45% yield.…”

“…In an effort to find some clues about the experimental results, HOMO-LUMO energy levels for dyes 1 ~ 6 were calculated at the HF-6-31G(d) level and those for dyes 22 ~ 25 ( Figure 5), which were developed by J. Ko, 15,19 were also calculated at the same level for comparison purposes.…”

A Zinc Porphyrin Sensitizer Modified with Donor and Acceptor Groups for Dye-Sensitized Solar Cells

“…The heart of this cell is a photoanode, consisting of a nanoporous TiO 2 film covered by a monolayer of photosensitizer. 6 Considerable effort has been devoted to the development of new and efficient sensitizers suitable for practical use, such as coumarin, [7][8][9] indoline, [10][11][12] oligoene, 13,14 thiophene, [15][16][17] triarylamine, [18][19][20] perylene, [21][22][23] cyanine, [24][25][26] phthalocyanine, 27 and hemicyanine derivatives.…”