Synthesis of Amphiphilic Ru(II) Heteroleptic Complexes Based on Benzo[1,2-b:4,5-b']dithiophene: Relevance of the Half-Sandwich Complex Intermediate and Solvent Compatibility

Maxence Urbani; María Medel; Sangeeta Amit Kumar; Mine Ince; Ashok N Bhaskarwar; David González-Rodríguez; Michael Grätzel; Mohammad Khaja Nazeeruddin; Tomás Torres

doi:10.1002/chem.201502417

Synthesis of Amphiphilic Ru(II) Heteroleptic Complexes Based on Benzo[1,2-b:4,5-b']dithiophene: Relevance of the Half-Sandwich Complex Intermediate and Solvent Compatibility

Chemistry. 2015 Nov 2;21(45):16252-65. doi: 10.1002/chem.201502417. Epub 2015 Sep 11.

Authors

Maxence Urbani^{1

2

3}, María Medel⁴, Sangeeta Amit Kumar^{5

6}, Mine Ince^{5

7}, Ashok N Bhaskarwar⁶, David González-Rodríguez⁴, Michael Grätzel⁵, Mohammad Khaja Nazeeruddin^{8

9}, Tomás Torres^{10

11}

Affiliations

¹ Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain). maxence.urbani@uam.es.
² Laboratory of Photonics and Interfaces, Institute of Chemical Sciences and Engineering, Swiss Federal Institute of Technology (EPFL), Station 6, 1015 Lausanne (Switzerland). maxence.urbani@uam.es.
³ Instituto Madrileño de, Estudios Avanzados (IMDEA)-Nanociencia c/Faraday, 9, Cantoblanco, 28049 Madrid (Spain). maxence.urbani@uam.es.
⁴ Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain).
⁵ Laboratory of Photonics and Interfaces, Institute of Chemical Sciences and Engineering, Swiss Federal Institute of Technology (EPFL), Station 6, 1015 Lausanne (Switzerland).
⁶ Ion Adsorption Laboratory, Department of Chemical Engineering, Indian Institute of Technology at Delhi, Hauz Khas, New Delhi, 110016 (India).
⁷ Mersin University, Department of Energy Systems Engineering, Faculty of Tarsus Technology, 33480, Mersin (Turkey).
⁸ Laboratory of Photonics and Interfaces, Institute of Chemical Sciences and Engineering, Swiss Federal Institute of Technology (EPFL), Station 6, 1015 Lausanne (Switzerland). mdkhaja.nazeeruddin@epfl.ch.
⁹ Group for Molecular Engineering of Functional materials Institute of Chemical Sciences and Engineering Swiss Federal Institute of Technology (EPFL), Station 6, 1015 Lausanne (Switzerland). mdkhaja.nazeeruddin@epfl.ch.
¹⁰ Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid (Spain). tomas.torres@uam.es.
¹¹ Instituto Madrileño de, Estudios Avanzados (IMDEA)-Nanociencia c/Faraday, 9, Cantoblanco, 28049 Madrid (Spain). tomas.torres@uam.es.

PMID: 26359935
DOI: 10.1002/chem.201502417

Abstract

The detailed synthesis and characterization of four ruthenium(II) complexes [RuLL'(NCS)2 ] is reported, in which L represents a 2,2'-bipyridine ligand functionalized at the 4,4' positions with benzo[1,2-b:4,5-b']dithiophene derivatives (BDT) and L' is 2,2'-bipyridine-4,4'-dicarboxylic acid unit (dcbpy) (NCS=isothiocyanate). The reaction conditions were adapted and optimized for the preparation of these amphiphilic complexes with a strong lipophilic character. The photovoltaic performances of these complexes were tested in TiO2 dye-sensitized solar cell (DSSC) achieving efficiencies in the range of 3-4.5 % under simulated one sun illumination (AM1.5G).

Keywords: dye/pigments; ligands; microwave chemistry; ruthenium; synthetic methods.