Synthesis of Alkynyl-Linked Phthalocyanine Dyads: Push–Pull Homo- and Heterodimetallic Bisphthalocyaninato Complexes

Maya, Eva M.; Vázquez, Purificación; Torres, Tomás

doi:10.1002/(sici)1521-3765(19990702)5:7<2004::aid-chem2004>3.3.co;2-g

Cited by 38 publications

(71 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The carboxyethynyl phthalocyanines TT22 , TT23 , TT40 , and TT43 were synthesized by means of two consecutive oxidation steps from the corresponding hydroxypropargyl derivatives: the reaction with the periodinane derivative IBX in DMSO afforded the corresponding formylethynyl derivatives, which were isolated and treated with NaClO 2 in water in the presence of sulfamic acid to yield the target compounds (see the Supporting Information). The synthesis of the corresponding mono‐ and bis(hydroxypropargyl) precursors were carried out by either a single or double Sonogashira coupling between a propargylic alcohol and the corresponding mono‐ or diiodo Pc derivatives, respectively 14…”

Section: J–v Characteristics Plotted As Wavelength Of Dsscs Sensitizementioning

confidence: 99%

Carboxyethynyl Anchoring Ligands: A Means to Improving the Efficiency of Phthalocyanine‐Sensitized Solar Cells

et al. 2012

Self Cite

View full text Add to dashboard Cite

Starre π‐konjugierte Brücken wie die Ethinylgruppe sind geeignet, um das π‐System eines Phthalocyanins effektiv an das Leitungsband von TiO2 zu koppeln. Eine Reihe von Zinkphthalocyanin‐Photosensibilisatoren mit Carboxyethinyl‐Ankergruppen wurde synthetisiert. Solarzellen, die mit der gezeigten Verbindung sensibilisiert wurden, zeigten Wirkungsgrade von 5.5 % und 6.1 % unter 100 (1 sun) bzw. 9.5 mW cm−2.

show abstract

Section: J–v Characteristics Plotted As Wavelength Of Dsscs Sensitizementioning

confidence: 99%

Carboxyethynyl Anchoring Ligands: A Means to Improving the Efficiency of Phthalocyanine‐Sensitized Solar Cells

et al. 2012

Self Cite

View full text Add to dashboard Cite

show abstract

“…CNC 2 H 4 SZnPc 1 was prepared by statistical condensation of 4‐(2‐cyanoethyl)thiophthalonitrile ( 3 ) and bis( p ‐ tert ‐octylphenoxy)phthalonitrile, to get the free base CNC 2 H 4 SH 2 Pc 4 , followed by zinc metalation (Scheme ). AcSPhC 2 ZnPc 2 was achieved by Sonogashira coupling of iodotri‐ tert ‐butylphthalocyaninate zinc (II) with 4‐ethynyl‐1‐acetylthiobenzene in a pretty good yield (Scheme ). For electrode sensitization, first CdS QDs were directly deposited on mesoporous TiO 2 substrate by SILAR method (see the Experimental Section for further details).…”

Section: Resultsmentioning

confidence: 99%

Synergistic Interaction of Dyes and Semiconductor Quantum Dots for Advanced Cascade Cosensitized Solar Cells

Blas‐Ferrando

Ortíz

González-Pedro

et al. 2015

Adv Funct Materials

View full text Add to dashboard Cite

Abstract.Here, we report a new procedure for the co-sensitization with quantum dots (QDs) and dyes for sensitized solar cell. Cascade co-sensitization of TiO 2 electrodes are obtained by the sensitization with CdS quantum dots (QDs) and zinc phthalocyanines (ZnPcs), in which ZnPcs containing sulfur atom have been specially designed to produce a cascade injection by attaching directly to QDs. This strategy causes a double synergetic interaction. This is the differentiating point of cascade co-sensitization in comparison with other approach in which dyes with conventional functionalization are employed, that pursue anchoring dyes to TiO 2 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 I ntroductionAn elegant strategy to improve the light-harvesting in photovoltaic devices is to use complementary light harvesters capable to produce panchromatic absorption. Here we have combined semiconductor quantum dots (QDs) and ad hoc designed phthalocyanines (Pcs) in order to prepare sensitized solar cells with enhanced efficiency. QDs are among potential key players in the next generation of photovoltaic devices [1] due to their low-cost solution-phase processability, large absorption cross sections, a spectrally tunable absorption onset (achieved via the quantum size effect), and enhanced multiple exciton generation or carrier multiplication. [2] After the first report on a certified QD solar cell, [3] a remarkable progress has been reached just in a couple of years obtaining certified power conversion efficiencies (PCEs) approaching 9%. [4] 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 3 On the other hand, Pcs are outstanding dye candidates in dye sensitized solar cells (DSSCs) due to their high extinction coefficient in the infrared spectral region and to their high thermal and chemical stabilities. [5] Pcs incorporated in DSSCs have achieved PCEs as high as 6.4 %, [6] still far away from the 12.75% PCE obtained by porphyrins, [7] their closest relatives. Light harvesting ability of QDs and Pcs can be enhanced by binding them, either covalent or supramolecular, producing a system capable to charge injection from both chromophores.However, the chemical combination of Pc rings to QDs has hardly been explored probably due to the difficulties to synthesize Pcs with the adequate anchoring groups. Until now just a few articles have been published where Pcs are covalently linked to QDs showing in most of the cases Förster resonance energy transfer (FRET) from QDs to Pcs. SiPc has been connected to CdSe QDs through axial ligation, [8] and also tetraminoZnPc [9] and unsymmetrically tris-tert-butyl-imidoZnPc [10] have been li...

show abstract

“…The Pc‐C 60 dyad 1 was prepared by a three‐step synthesis starting from the unsymmetrical tri‐ tert ‐butyl iodo Pc,13 which was subjected to a Sonogashira coupling reaction with 4‐ethynylbenzaldehyde to give the benzaldehyde‐substituted Pc 2 in 92 % yield. Reaction of the latter compound with C 60 fullerene in the presence of N ‐methylglycine afforded the dyad 1 in 36 % yield as a racemic mixture at the methine pyrrolidine carbon atom (Scheme ).…”

Section: Methodsmentioning

confidence: 99%

Highly Conductive Supramolecular Nanostructures of a Covalently Linked Phthalocyanine–C₆₀ Fullerene Conjugate

et al. 2008

Self Cite

View full text Add to dashboard Cite

Leitfähige Oberflächen: Ein kovalent verknüpftes Konjugat eines Phthalocyanins mit C60‐Fulleren (1; siehe Bild) organisiert sich auf Graphit‐ oder graphitähnlichen Oberflächen in Form supramolekularer Fasern und Filme. Diese Nanostrukturen, deren elektrische Eigenschaften durch Leitfähigkeits‐Rasterkraftmikroskopie charakterisiert wurden, zeigen eine herausragende elektrische Leitfähigkeit auf der Nanoskala.

show abstract

Synthesis of Alkynyl-Linked Phthalocyanine Dyads: Push–Pull Homo- and Heterodimetallic Bisphthalocyaninato Complexes

Cited by 38 publications

References 0 publications

Carboxyethynyl Anchoring Ligands: A Means to Improving the Efficiency of Phthalocyanine‐Sensitized Solar Cells

Carboxyethynyl Anchoring Ligands: A Means to Improving the Efficiency of Phthalocyanine‐Sensitized Solar Cells

Synergistic Interaction of Dyes and Semiconductor Quantum Dots for Advanced Cascade Cosensitized Solar Cells

Highly Conductive Supramolecular Nanostructures of a Covalently Linked Phthalocyanine–C₆₀ Fullerene Conjugate

Contact Info

Product

Resources

About

Synthesis of Alkynyl-Linked Phthalocyanine Dyads: Push–Pull Homo- and Heterodimetallic Bisphthalocyaninato Complexes

Cited by 38 publications

References 0 publications

Carboxyethynyl Anchoring Ligands: A Means to Improving the Efficiency of Phthalocyanine‐Sensitized Solar Cells

Carboxyethynyl Anchoring Ligands: A Means to Improving the Efficiency of Phthalocyanine‐Sensitized Solar Cells

Synergistic Interaction of Dyes and Semiconductor Quantum Dots for Advanced Cascade Cosensitized Solar Cells

Highly Conductive Supramolecular Nanostructures of a Covalently Linked Phthalocyanine–C60 Fullerene Conjugate

Contact Info

Product

Resources

About

Highly Conductive Supramolecular Nanostructures of a Covalently Linked Phthalocyanine–C₆₀ Fullerene Conjugate