Molecular Engineering of Zinc Phthalocyanines with Phosphinic Acid Anchoring Groups

López‐Duarte, Ismael; Wang, Mingkui; Humphry‐Baker, Robin; Ince, Mine; Martínez‐Díaz, M. Victoria; Nazeeruddin, Mohammad Khaja; Torres, Tomás; Grätzel, Michaël

doi:10.1002/anie.201105950

Cited by 92 publications

(46 citation statements)

References 23 publications

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“…However, the phosphinic acid anchor was shown to have stronger binding properties than the carboxylic one, which is a major advantage to improve the durability of a DSSC. 210 Odobel et al reported a series of phosphonato-and carboxyphenyl functionalized porphyrin dyes (H2-pTCPP, p-TPPP, and m-TPPP, see Figure 13 and Table 1, entry 4) and claimed that the nature of the functional group (−PO 3 H or −COOH) has a little influence toward the performance of the cells in comparison with the substitution position of the anchoring group. 211 It is indeed known and well-established that apart from the intrinsic nature of the binding group the substitution position have a drastic influence toward the performances of the cell, caused by changes in both the binding geometry of the dye onto the TiO 2 surface and electronic interactions between dye and TiO 2 (mediated through the spacer linking binding group and porphyrin).…”

Section: A4-type Design For Meso-subsitutedmentioning

confidence: 99%

Meso-Substituted Porphyrins for Dye-Sensitized Solar Cells

et al. 2014

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Section: A4-type Design For Meso-subsitutedmentioning

confidence: 99%

Meso-Substituted Porphyrins for Dye-Sensitized Solar Cells

et al. 2014

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“…[2][3][4][5][6][7][8] Among donor groups, triphenylamine and its derivatives have shown promise in the development of DSSCs owing to their nonplanar structure suppressing the dye aggregation. [11] Recently, pyridine, [12] phosphinic acid, [13] and 8-hydroxylquinoline [10] have been explored as anchoring groups; nevertheless, the efficiencies of DSSCs based on these acceptors still lag behind that of cyanoacrylic acid counterparts. In particular, the introduction of cyanoacrylic acid as electron-accepting unit has witnessed the rapid development of organic dyes as sensitizers.…”

Section: Dedication To Professor Klaus Müllen On the Occasion Of His mentioning

confidence: 99%

Stable Dyes Containing Double Acceptors without COOH as Anchors for Highly Efficient Dye‐Sensitized Solar Cells

et al. 2012

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“…20 We reported a novel peripherally substituted 2, 3,9,10,16,17,23,24-octatosylamino-phthalocyanine which acts as a viable chromogenic anion chemosensor with high affinity towards uoride ions. 21 Suitable modication of Pcs with functional ligands results in a signicant change of their optical properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photophysical characterization of dimethylamine-derived Zn(ii)phthalocyanines: exploring their potential as selective chemosensors for trinitrophenol

et al. 2015

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We report a novel synthetic approach, with good yields, for the synthesis of selective dimethylaminesubstituted phthalonitriles (1-3) in the presence of triethyl phosphite and dimethylformamide at 160 C.The peripherally modified dimethylamine substituted Zn(II)phthalocyanines (ZnPc1-3) with varied numbers and positions of dimethylamine groups were prepared for a systematic investigation of the effect of the substituents on their electronic and spectroscopic properties. Compounds show strong aggregation behaviour in methanol and this behaviour decreases with the increase of the alkyl chain length of the alcohol solvents (i.e., from methanol to octanol). The fluorescence quantum yields of ZnPc1-3 showed an excellent correlation with the extent of the molecular aggregation. The versatility of the ZnPc1-5 compounds possessing both electron donating and electron withdrawing substituents at their periphery is investigated towards the detection of nitroaromatic compounds (NACs) in solution and in the vapour phase. It was found that ZnPc1-5 exhibit high selectivity towards trinitrophenol (TNP). A good linearity of fluorescence detection using ZnPc3 as the fluorescent probe was observed in the concentration range of 50 Â 10 À6 to 450 Â 10 À6 M in chloroform, with a detection limit (LOD) of 11 AE 2 ppm. Stern-Volmer (SV) and DFT studies reveal that the fluorescence quenching behaviour occurs through photo-induced electron transfer from the excited state of ZnPcs to TNP with static quenching behaviour occurring in a predominant fashion. The formation of a porous morphology of ZnPc3 thin films promotes high selectivity and accessibility to TNP vapours (7.7 Â 10 À3 ppb).

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Molecular Engineering of Zinc Phthalocyanines with Phosphinic Acid Anchoring Groups

Cited by 92 publications

References 23 publications

Meso-Substituted Porphyrins for Dye-Sensitized Solar Cells

Meso-Substituted Porphyrins for Dye-Sensitized Solar Cells

Stable Dyes Containing Double Acceptors without COOH as Anchors for Highly Efficient Dye‐Sensitized Solar Cells

Synthesis and photophysical characterization of dimethylamine-derived Zn(ii)phthalocyanines: exploring their potential as selective chemosensors for trinitrophenol

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