Synthesis and characterization of novel thieno[3,2-b]thiophene based metal-free organic dyes with different heteroaromatic donor moieties as sensitizers for dye-sensitized solar cells

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• 作者：Sara S.M. Fernandes^a ; M. Cidá ; lia R. Castro^a ; I. Mesquita^b ; L. Andrade^b ; A. Mendes^b ; M. Manuela M. Raposo^a ; ^{mfox@quimica.uminho.pt" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Dye sensitized solar cells ; Heterocyclic organic dye ; Metal-free thieno[3 ; 2-b]thiophene dye ; Cyanoacetic acid anchoring group ; Heterocyclic donor groups ; Co-adsorption
• 刊名：Dyes and Pigments
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：136
• 期：Complete
• 页码：46-53
• 全文大小：759 K

文摘

Four novel heterocycle dyes 3a-d were synthesized in order to study the variations produced in the optical, electronic and photovoltaic properties by substitution of different electron-rich heterocyclic groups to the thieno[3,2-b]thiophene system. The final push-pull conjugated dyes 3a-d were synthesized by Suzuki-Miyaura coupling reaction followed by Knoevenagel condensation of the corresponding aldehyde precursors with cyanoacrylic acid 2a-d. These new push-pull systems are based on a thieno[3,2-b]thiophene spacer, a cyanoacetic acid anchoring group and several electron-rich heterocycles (thiophene, pyrrole and furan) as donor groups. The multidisciplinary study concerning the optical, redox and photovoltaic characterization of the dyes reveals that compound 3b bearing a hexyl-bithiophene donor group/heterocyclic spacer exhibits the best overall conversion efficiency (2.49%) as sensitizer in nanocrystalline TiO₂ dye sensitized solar cells. Co-adsorption studies between N719 and 3b revealed that upon addition of N719 co-adsorbent, the optimized cell efficiencies were improved by 16–77%. The best efficiency was 4.40%, corresponding to 54% of the photovoltaic performance of the N719-based DSSC fabricated and measured under similar conditions.