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Introducing rigid $π$ $π$ -conjugated peripheral substituents in phthalocyanines for DSSCs

Departamento de Química Orgánica, Facultad de Ciencias, C/Francisco Tomás y Valiente 7, Universidad, Autónoma de Madrid, 28049 Madrid, Spain

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Esmeralda Caballero

Departamento de Química Orgánica, Facultad de Ciencias, C/Francisco Tomás y Valiente 7, Universidad, Autónoma de Madrid, 28049 Madrid, Spain

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M. Victoria Martínez-Díaz

Departamento de Química Orgánica, Facultad de Ciencias, C/Francisco Tomás y Valiente 7, Universidad, Autónoma de Madrid, 28049 Madrid, Spain

E-mail Address: victoria.martinez@uam.es

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Mohammad Khaja Nazeeruddin

Group for Molecular Engineering of Functional Materials, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne (EPFL), Rue de l'Industrie 17, 1951 Sion, Switzerland

E-mail Address: mdkhaja.nazeeruddin@epfl.ch

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Michael Grätzel

Laboratory of Photonics and Interfaces, Institute of Chemical Sciences and Engineering, École Polytechnique, Fédérale de Lausanne (EPFL), Station 6, 1015 Lausanne, Switzerland

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, and

Tomas Torres

Departamento de Química Orgánica, Facultad de Ciencias, C/Francisco Tomás y Valiente 7, Universidad, Autónoma de Madrid, 28049 Madrid, Spain

IMDEA-Nanociencia, C/Faraday 9, Ciudad Universitaria de Cantoblanco, 28049 Madrid, Spain

E-mail Address: tomas.torres@uam.es

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https://doi.org/10.1142/S1088424616501121Cited by:3 (Source: Crossref)

Abstract

A new carboxy-Zn(II)phthalocyanine bearing rigid 2,6-diarylphenyl peripheral substituents linked to the macrocycle through alkynyl spacers has been prepared by a convergent approach, which implies a triple Sonogashira coupling between the formyltriiodoZnPc and the corresponding terminal alkyne. Indeed, the introduction of this type of $π$ $π$ -conjugated peripheral substituents accounts for a remarkable red shift of the phthalocyanine Q-band until ca. 700 nm. However, aggregation phenomena could not be supressed and may explain the moderate overall efficiencies achieved with these devices.

Dedicated to Professor Tomás Torres on the occasion of his 65th birthday

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