Mine Ince

Molecular Engineering of Zinc Phthalocyanines with Phosphinic Acid Anchoring Groups

Keywords: dyes ; pigments ; light harvesting ; phthalocyanines ; sensitizers ; solar cells ; Sensitized Solar-Cells ; Photovoltaic Cells ; Tio2 Films ; Performance ; Efficiency ; Dyes Reference EPFL-ARTICLE-176099doi:10.1002/anie.201105950View record in Web of Science Record created on 2012-04-05, modified on 2016-08-09

Liquid crystalline phthalocyanine–fullerene dyads

Two phthalocyanine–C60 dyads 1 and 2 incorporating either a rigid or a flexible spacer between the phthalocyanine and fullerene units, respectively, have been prepared. Indeed, the nature of the spacer has proven to play an important role in the liquid crystalline properties of these compounds. Phthalocyanine–C60 dyad 2, containing a flexible spacer, self-organizes in columnar stacks within a rectangular arrangement. On the other hand, dyad 1 does not present mesomorphic properties on its own, but forms columnar hexagonal mesophases when blended with equimolar amounts of an intrinsically mesomorphic phthalocyanine.

Sterically Hindered Phthalocyanines for Dye‐Sensitized Solar Cells: Influence of the Distance between the Aromatic Core and the Anchoring Group

A new phthalocyanine (Pc) bearing bulky peripheral substituents and a carboxylic anchoring group directly attached to the macrocycle has been prepared and used as a sensitizer in DSSCs, reaching 5.57% power conversion efficiency. In addition, an enhanced performance for the TT40 dye, previously reported by us, was achieved in optimized devices, obtaining a new record efficiency with Pc-sensitized cells.

Immobilizing NIR absorbing azulenocyanines onto single wall carbon nanotubes—from charge transfer to photovoltaics

In this fundamental study, the supramolecular interactions between SWNTs and either symmetrical Zn(II) octa-tert-butylazulenocyanine 1 or a Zn(II) azulenocyanine-phthalocyanine 2 bearing a pyrene unit have been evaluated. The synthetic protocol allowed for the preparation of unsymmetrical azulenocyanine-phthalocyanine molecules, which incorporate reactive hydroxyl functional groups useful for the preparation of more elaborate derivatives, that is, the pyrene containing derivative 2 by an esterification reaction. To shed light onto the mutual interactions between 1 or 2 and SWNT, stable suspensions of SWNT in a mixture of 25% THF and 75% DMF were titrated with variable amounts of 1 or 2. These assays indicate a successful immobilization of azulenocyanine derivatives 1 or 2 onto SWNTs to yield the supramolecular hybrids SWNT/1 and SWNT/2. In this light, the physico-chemical properties of 1 and 2 as well as those of SWNT/1 and SWNT/2 were investigated. From these we conclude strong interactions in the ground state, and a rapid charge separation in the excited state of SWNT/1 or SWNT/2. The accordingly formed radical ion pair states decay with lifetimes of 124 and 137 ps for SWNT/1 and SWNT/2, respectively. Finally, SWNT/1 and SWNT/2 were integrated into photoelectrochemical cells, revealing a response throughout the visible and near-infrared with a moderate IPCE maxima of 2.5%.

Convergent Synthesis of Near‐Infrared Absorbing, “Push–Pull”, Bisthiophene‐Substituted, Zinc(II) Phthalocyanines and their Application in Dye‐Sensitized Solar Cells

Zinc(II) phthalocyanine dyes that contain triarylamine-terminated bisthiophene and hexylbisthiophene groups have been synthesized by a convergent approach by using carboxytriiodo-ZnPc as a precursor. Further transformation of the iodo groups by a Pd-catalyzed reaction allowed easy preparation of further extended π-conjugated carboxy-ZnPcs. These dyes have been used as sensitizers in dye-sensitized solar cells, which exhibit a panchromatic response and moderate overall efficiencies.

Peripherally and Axially Carboxylic Acid Substituted Subphthalocyanines for Dye-Sensitized Solar Cells

A series of subphthalocyanines (SubPcs) bearing a carboxylic acid group either at the peripheral or axial position have been designed and synthesized to investigate the influence of the COOH group positions on the dye-sensitized solar cell (DSSC) performance. The DSSC devices based on SubPcs with axially substituted carboxylic acid groups showed low photovoltaic performance, whereas peripherally substituted one exhibited higher power conversion efficiency owing to improved injection from LUMO of SubPcs to the TiO2 conduction band.

Synthesis of subphthalocyanines as probes for the accessibility of silica nanochannels

The synthesis of a new subphthalocyanine is reported. Its structural and photophysical properties are ideal for probing the accessibility of arrays of silica nanochannels.

Construction and amperometric biosensing performance of a novel platform containing carbon nanotubes-zinc phthalocyanine and a conducting polymer

A novel glucose oxidase (GOx) based amperometric biosensor utilizing a conducting polymer (CP), multi walled carbon nanotubes (MWCNTs) and a novel water soluble zinc phthalocyanine (ZnPc) was constructed. For this purpose, a novel ZnPc was synthesized to examine the role of being a part of support material for enzyme deposition. High water solubility was achieved with the introduction of tetra quaternized imidazolyl moieties at the peripheral positions of phthalocyanine. In order to fabricate the proposed biosensor, a graphite electrode was firstly modified with poly[9,9-di-(2-ethylhexyl)- fluorenyl-2,7-diyl] end capped with N,N-Bis(4- methylphenyl)-4-aniline (PFLA) and MWCNTs. Then, GOx was co-immobilized with ZnPc onto the modified surface. To the best our knowledge, a sensor design which combines conjugated polymer/MWCNTs/ZnPc was attempted for the first time and this approach resulted in improved biosensor characteristics. The constructed biosensor showed a linear response for glucose between 0.025-1.0mM with a detection limit of 0.018mM. KMapp and sensitivity values were calculated as 0.53mM and 82.18μAmm-1cm-2, respectively. Moreover, scanning electron microscopy (SEM) and cyclic voltammetry (CV) techniques were used to investigate the surface modifications. Finally, fabricated biosensor was tested on beverages for glucose detection successfully.

Investigation of in vitro PDT activities of zinc phthalocyanine immobilised TiO2 nanoparticles

Phthalocyanines (Pcs) are commonly used as Photosensors (PSs) in Photodynamic Therapy (PDT) applications due to their intense absorption in the far red-near IR spectral region with a high extinction coefficient and high ability for generating singlet oxygen. Pcs targetspecifically tumors, and do not show any considerable toxic effects under the absence of light. In particular, their chemical versatility has allowed the introducion a number of substituent at the periferal or axial positions which provide modulating photophysical properties, increases the solubility of these compounds in organic solvents. Nanoparticles increase the bioavailability, stability, and transport of PSs to target tissue. TiO2 nanoparticles are prefered in these applications because of their non toxic, low cost and high chemical stability properties. In our study, a Zinc Phthalocyanine (ZnPc) was used as a photosensor. The design of ZnPc integrated TiO2 nanoparticles is intended to make PSs a more effective PDT agent. With the aim to examine the nuclear imaging/treatment potentials of ZnPc and ZnPc-TiO2 in hepatocellular carcinoma (HepG2), colorectal adenocarcinoma (HT29) tumor and human healthy lung (WI38) cell lines in vitro study ZnPc and TiO2-ZnPc were also labeled with 131I. It is determined that 131I-ZnPc-TiO2 nanoparticle show a potential as an agent for the imaging/treatment of hepatocellular cancer by in vitro. The toxicity studies revealed that TiO2 nanoparticle decreases the toxicity of ZnPc. In vitro PDT results show that TiO2-ZnPc has a potential as a PDT agent in colon tumor treatment. Consequently, synthesized ZnPc and ZnPc-TiO2 could be promising candidates as theranostic agents.

Effect of Peripheral Substitution on the Performance of Subphthalocyanines in DSSCs

A series of six new subphthalocyanines (SubPcs) bearing an ethynylcarboxyphenyl anchoring unit and decorated with a variety of substituents at the peripheral position of the macrocycle have been synthesized in order to investigate the effect of the peripheral substituent on the performance of dye-sensitized solar cells.