ArticleMacromolecular rapid communications2025
Versatile Direct (Hetero)Arylation Polymerization of Electro-Deficient Unsubstituted Thiazolo[5,4-d]Thiazole: A Tool to Lower the LUMO Level.
Article in Macromolecular rapid communications, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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Who cites it
2 citing papers in PubMed.
- Synthetic Method-Defect Correlations in Aldol Polycondensation: From Model Reactions to an n-Type Thiazolothioazole Copolymer.Journal of the American Chemical Society · 2026Article
- Versatile Direct (Hetero)Arylation Polymerization of Electro-Deficient Unsubstituted Thiazolo[5,4-d]Thiazole: A Tool to Lower the LUMO Level.Macromolecular rapid communications · 2025Article
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10 authors.
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Abstract
A series of novel conjugated semiconducting polymers based on the unsubstituted thiazolo[5,4-d]thiazole (TzTz) unit is synthesized using atom-economic and environmentally friendly direct (hetero)arylation polymerization (DHAP). The versatility of the proposed polymerization conditions, employing a non-chlorinated and moderately toxic solvent and cooperative palladium/copper bimetallic catalytic system, is demonstrated through the use of seven comonomers with varying electron-withdrawing strength: 2,2'-bithiophene (BT), 6,7-difluoroquinoxaline (Qx), thieno[3,4-c]pyrrole-4,6(5H)-dione (TPD), 5,6-difluorobenzo[c][1,2,5]thiadiazole (BTD), isoindigo (IID), para-azaquinodimethane (AQM) and 2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (DPP). The resulting TzTz-based copolymers exhibit optical bandgaps between 1.5 and 2.0 eV with HOMO/LUMO energy levels spanning from -5.2/-3.3 eV to -5.4/-3.9 eV. They all show satisfactory thermal stability for electronic applications (Td = 300-360 °C). Notably, TzTz-based copolymers are observed they generally exhibit improved backbone planarity and deeper LUMO levels than their thiophene derivatives. A synthesis tool to finely lower the LUMO levels of next-generation A-A' copolymers in view of increasing the performance and air-stability of doped organic electronics is believed to be provided by this work.
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