Commercially viable porphyrinoid dyes for solar cells

Radivojevic, Ivana; Varotto, Alessandro; Farley, Christopher; Drain, Charles Michael

doi:10.1039/c0ee00009d

Cited by 48 publications

(42 citation statements)

References 203 publications

(222 reference statements)

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“…Pc organic dyes have energy band gaps that are well-matching the incident solar spectrum. 9 However, the use of Pcs in low-cost solar cells faces complications because of poor solubility in organic solvents and narrow absorption bandwidths in the red (Q-band) and ultraviolet (B-band) wave-lengths. 9 Pcs have been used in bulk heterojunction (BHJ) solar cells.…”

Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

“…9 However, the use of Pcs in low-cost solar cells faces complications because of poor solubility in organic solvents and narrow absorption bandwidths in the red (Q-band) and ultraviolet (B-band) wave-lengths. 9 Pcs have been used in bulk heterojunction (BHJ) solar cells. 49,126,172,173 Some solar cell designs contain Zn(II) and Cu(II) Pc complexes and also contain various C 60 derivatives, where vapour-deposition techniques are used to make specified layers.…”

Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

“…Functional groups on the periphery of structurally rigid porphyrinoids provide topological diversity, making these dyes well suited for the engineering of supramolecular materials. 9 …”

Section: Introductionmentioning

confidence: 99%

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Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

et al. 2016

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Porphyrinoids are robust heterocyclic dyes studied extensively for their applications in medicine and as photonic materials because of their tunable photophysical properties, diverse means of modifying the periphery, and the ability to chelate most transition metals. Commercial applications include their use as phthalocyanine dyes in optical discs, porphyrins in photodynamic therapy, and as oxygen sensors. Most applications of these dyes require exocyclic moieties to improve solubility, target diseases, modulate photophysical properties, or direct the self-organization into architectures with desired photonic properties. The synthesis of the porphyrinoid depends on the desired application, but the de novo synthesis often involves several steps, is time consuming, and results in low isolated yields. Thus, the application of core porphyrinoid platforms that can be rapidly and efficiently modified to evaluate new molecular architectures allows researchers to focus on the design concepts rather than the synthesis methods, and opens porphyrinoid chemistry to a broader scientific community. We have focused on several widely available, commercially viable porphyrinoids as platforms: meso-perfluorophenylporphyrin, perfluoro-phthalocyanine, and meso-perfluorophenylcorrole. The perfluorophenylporphyrin is readily converted to the chlorin, bacteriochlorin, and isobacteriochlorin. Derivatives of all six of these core platforms can be efficiently and controllably made via mild nucleophilic aromatic substitution reactions using primary S, N, and O nucleophiles bearing a wide variety of functional groups. The remaining fluoro groups enhance the photo and oxidative stability of the dyes and can serve as spectroscopic signatures to characterize the compounds or in imaging applications using 19F NMR. This review provides an overview of the chemistry of fluorinated porphyrinoids that are being used as a platform to create libraries of photo-active compounds for applications in medicine and materials.

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Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

Section: Substituted Fluorinated Porphyrinoids For Application In Matmentioning

confidence: 99%

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Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

et al. 2016

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“…[10][11][12][13] Key to the increase of efficiency in porphyrin-based DSSCs was the development of non-aggregating porphyrins with high extinction coefficient absorption spectra reaching into the NIR, such as push-pull architecture porphyrin 1 or π-extended porphyrin 2. [10, 14,15] However, the syntheses of these and related systems is complex and inefficient, inhibiting the progress in the understanding of the correlation of molecular design and photovoltaic performance by testing a wider range of derivatives that might include a range of commercially viable porphyrinoid dyes, [16] or hydroporphyrins, nature's light harvesters. [17] Recently tested hydroporphyrins were promising but they were also prepared by multi-step, non-trivial total syntheses.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Introduction of carboxylic ester and acid functionalities to meso-tetrakis(pentafluorophenyl)porphyrin and their limited electronic effects on the chromophore

et al. 2015

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Please cite this article as: Hewage N, Yang B, Agrios AG, Brückner C, Introduction of Carboxylic Ester and Acid Functionalities to meso-Tetrakis(pentafluorophenyl)porphyrin and their Limited Electronic Effects on the Chromophore, Dyes and Pigments (2015), AbstractAlkyl-or aryl-carboxylic acid-functionalized porphyrinic dyes are sought after because of their propensity to adhere strongly to many metal oxide surfaces as required for their application as, for instance, sensitizers in dye-sensitized solar cells (DSSCs), in air purification, or chemosensing systems. The S N Ar reaction of the pentafluorophenyl group is a versatile method to introduce functionality into meso-pentafluorophenyl-substituted porphyrins. The conditions to introduce one through four alkyl-or aryl-carboxyl functionalities using mercaptopropionate or 3,4-dihydroxybenzoate esters, respectively, are explored, and the regioisomeric products are spectroscopically characterized. Their saponification to the corresponding carboxylic acids was studied. By experimental determination of their optical properties (absorption and emission spectroscopy) and their frontier orbital positions by cyclic voltammetry, we demonstrate the minimal electronic influence this derivatization method has on the chromophore.

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“…In particular phthalocyanines [6][7][8][9], porphyrins [10][11][12][13], and chlorins immobilized on polycrystalline titanium dioxide were investigated and studied with respect to achieve technically and economically reasonable dye sensitized solar cells [14][15][16][17][18][19][20][21][22][23][24]. For self-assembling on titanium dioxide or similar metal oxide surfaces compounds are required which bear carboxylic-, phosphonic-or sulfonic acid functionalities for covalent linking to the surface.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel porphyrin and chlorin phosphonic acids and their immobilization on metal oxides

Erbacher

Montforts

2011

J. Porphyrins Phthalocyanines

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In this study an easy and flexible access to porphyrin and chlorin phosphonic acids is presented. Novel types of phosphonic acid terminated porphyrins and chlorins were synthesized starting from commercially available red blood pigment hemin chloride. Phosphonic acid groups were linked to the porphyrinoids by amide coupling via appropriate spacer moieties. Self-assembled monolayers of the synthesized phosphonates on mesoporous TiO 2 electrodes of approximately 3 µm thickness were formed. Surface concentrations in a range of 1 to 4 × 10 -8 mol.cm -2 could be determined by UV-vis spectroscopy.

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Commercially viable porphyrinoid dyes for solar cells

Cited by 48 publications

References 203 publications

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

Introduction of carboxylic ester and acid functionalities to meso-tetrakis(pentafluorophenyl)porphyrin and their limited electronic effects on the chromophore

Synthesis of novel porphyrin and chlorin phosphonic acids and their immobilization on metal oxides

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