Organic Chromophores Based on a Fused Bis‐Thiazole Core and Their Application in Dye‐Sensitized Solar Cells. Issue 10 (18th February 2013)

• Record Type: Journal Article
• Authors: Dessì, Alessio; Barozzino Consiglio, Gabriella; Calamante, Massimo; Reginato, Gianna; Mordini, Alessandro; Peruzzini, Maurizio; Taddei, Maurizio; Sinicropi, Adalgisa; Parisi, Maria Laura; Fabrizi de Biani, Fabrizia; Basosi, Riccardo; Mori, Riccardo; Spatola, Michele; Bruzzi, Mara; Zani, Lorenzo
• Is Part Of: European journal of organic chemistry. Issue 10(2013)
• Page Start: 1916
• Page End: 1928
• Publication Date: 2013-02-18
• Subjects: Synthetic methods -- Dyes/pigments -- Fused‐ring systems -- Photochemistry -- Sensitizers -- Solar cells; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201629
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Four new D‐π‐A organic dyes incorporating either a thiazolo[5, 4‐ d ]thiazole bicyclic system (TTZ1 –2 ) or a benzo[1, 2‐ d :4, 5‐ d′ ]bisthiazole tricyclic unit (BBZ1 –2 ) have been synthesized and fully characterized. The key steps of the synthesis include an efficient MW‐assisted preparation of the thiazolo[5, 4‐ d ]thiazole core and selective functionalization of two different dihalothienyl derivatives through Suzuki coupling. All the compounds showed photo‐ and electrochemical properties compatible with their employment in dye‐sensitized solar cells. In addition, their electronic structure and transitions were investigated by means of TD‐DFT calculations. Dye‐sensitized solar cells fabricated with dyeTTZ1 yielded an average power conversion efficiency corresponding to 43 and 60 % of the performances recorded under the same conditions for cells containing reference dyesN3 andD5, respectively. Efficiency measurements and electrochemical impedance spectroscopy (EIS) experiments indicated that use of chenodeoxycholic acid (CDCA) as a co‐adsorbent was beneficial to disrupt dye‐dye interactions and slow down recombination processes within the cells, thus allowing power conversion efficiencies up to 3.53 % to be obtained. Abstract : Four D‐π‐A dyes incorporating fused‐heterocyclic ring systems, such as thiazolothiazoles and benzobisthiazoles, have been synthesized and characterized. Their incorporation into dye‐sensitized solar cells yielded devices with power conversion efficiencies up to 3.53 %. The average efficiencies of the cells were 43 and 60 % those of cells containing the reference dyesN3 andD5, respectively.