Suchergebnisse

This document is the unedited author's version of a Submitted Work that was subsequently accepted for publication in Organic Letters, copyright © American Chemical Society after peer review. To access the final edited and published work, see http://pubs.acs.org/doi/abs/10.1021/ol503557c ; A new design of non-aggregated zinc(II) carboxyphthalocyanines with potential application in dye-sensitized solar cells has been developed. It is based on the introduction of bulky and rigid aryl groups at three α positions of the macrocycle. The synthesis has been carried out following a convergent route in which the bulky aryl groups are introduced by Suzuki-Miyaura cross-coupling reaction on a preformed triiodophthalocyanine derivative. Two regioisomers of this α-triaryl-β-car-boxyphthalocyanine could be isolated by column chromatography ; Financial support is acknowledged from European Union within the FP7-ENERGY-2012-1 framework, GLOBALSOL project, Proposal No 309194-2 and from the Spanish MEC (CTQ2011- 24187/BQU) and MICINN (PRI-PIBUS-2011-1128)

This is the peer reviewed version of the following article:Chemistry - A European Journal 22.13 (2016): 4369-4373, which has been published in final form at http://dx.doi.org/10.1002/chem.201600166. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving ; Phthalocyanines (Pcs) are used as sensitizers in dye-sensitized solar cells (DSSCs) because of their stability and intense absorption in the red and near-IR regions. Impressive progress has been made in photovoltaic efficiencies by introduction of bulky peripheral substituents to help suppress macrocycle aggregation. To reach benchmark efficiencies reported for other related dyes, new designs need to be explored. Single carboxy-ZnPc regioisomers substituted at the non-peripheral positions by rigid aryl groups have now been studied, which has shed light on the influence of steric hindrance and/or orientation of the substituent around the anchoring group on the photovoltaic response. The regioisomer bearing the aryl group far away from the anchoring group produces a more effective sensitization of the TiO2 films and higher short-circuit photocurrent density (Jsc). Taking advantage of the good photovoltaic performance in the near-IR region of this ZnPc, it was combined with another appropriate dye for panchromatic sensitization of the mesoporous photoelectrode and an increase of the overall device efficiency ; Financial support from the European Union (FP7-ENERGY-2012- 1 framework, GLOBASOL project, Proposal No 309194-2), from the Spanish MINECO (CTQ2014-52869-P), Comunidad de Madrid (FOTOCARBON S2013/MIT-2841), and MECD (F.P.U. fellowship to L.T.) is gratefully acknowledged