5-Alkyl-8-hydroxyquinolines: Synthesis and Application in Dye-Sensitized Solar Cells
The use of co-adsorbents in dye-sensitized solar cells (DSCs) increases both the power-conversion efficiency and long-term stability of these devices. Co-adsorbents usually consist of a hydrophobic moiety attached on a carboxylic or phosphoric acid terminal anchoring group, which chemisorbs on the semiconductor surface. In this work, the synthesis of a new family of 8-quinolinol derivatives bearing alkyl chains of variable length at the 5-position is described and their comparative efficiency as effective bidentate co-adsorbents in DSCs is evaluated. The key step towards their straightforward modular synthesis is a Suzuki coupling between 5-chloro-8-methoxyquinoline and alkyltrifluoroborates. The new compounds showed better performance as co-adsorbents in terms of cell efficiency as compared to their alkylcarboxylic acid analogues, with the best results obtained from the derivative bearing the longer dodecyl alkyl chain.
Manthou, Victoria S.,Perganti, Dorothea,Rotas, Georgios,Falaras, Polycarpos,Vougioukalakis, Georgios C.
A SHORT AND CONVENIENT SYNTHESIS OF 5-ALKYL SUBSTITUTED 8-HYDROXYQUINOLINES
5-Chloro-8-methoxyquinoline undergoes rapid and reversible lithium-halogen exchange reaction with alkyllithiums to yield 5-substituted derivatives indirectly, whereas the reaction with phenyllithium is slower and 5-alkyl substituted compounds are formed by the direct addition of alkyl halides.
Hojjatie, Massoud,Muralidharan, Subramaniam,Dietz, Mark L.,Freiser, Henry
p. 2273 - 2282
(2007/10/02)
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