A Convenient Synthesis of Pentaporphyrins and Supramolecular Complexes with a Fulleropyrrolidine.

Joana I T Costa; Andreia S F Farinha; Filipe A Almeida Paz; Augusto C Tomé

doi:10.3390/molecules24173177

A Convenient Synthesis of Pentaporphyrins and Supramolecular Complexes with a Fulleropyrrolidine.

Joana I T Costa, Andreia S F Farinha, Filipe A Almeida Paz, Augusto C Tomé

King Abdullah University of Science and Technology

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

A simple and straightforward synthesis of diporphyrins and pentaporphyrins is reported here. The supramolecular interactions of the new porphyrin derivatives with C60 and PyC60 (a pyridyl [60]fulleropyrrolidine) were evaluated by absorption and fluorescence titrations in toluene. While no measurable modifications of the absorption and fluorescence spectra were observed upon addition of C60 to the porphyrin derivatives, the addition of PyC60 to the corresponding mono-Zn(II) porphyrins resulted in the formation of Zn(porphyrin)-PyC60 coordination complexes and the binding constants were calculated. Results show that the four free-base porphyrin units in pentaporphyrin 6 have a significant contribution in the stabilization of the 6-PyC60 complex. The crystal and molecular features of the pentaporphyrin Zn5 were unveiled using single-crystal X-ray diffraction studies.

Original language	English (US)
Pages (from-to)	3177
Journal	Molecules (Basel, Switzerland)
Volume	24
Issue number	17
DOIs	https://doi.org/10.3390/molecules24173177
State	Published - Sep 1 2019

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: Thanks are due to the University of Aveiro and Fundação para a Ciência e a Tecnologia (FCT, Portugal) for the financial support to the project PTDC/QEQ-QOR/6160/2014 and the research units UID/QUI/00062/2019 and UID/CTM/50011/2019 through national funds and where applicable co-financed by the FEDER, within the PT2020 Partnership Agreement, and also to the Portuguese NMR Network.

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10.3390/molecules24173177

https://repository.kaust.edu.sa/bitstream/10754/656701/1/molecules-24-03177.pdf

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title = "A Convenient Synthesis of Pentaporphyrins and Supramolecular Complexes with a Fulleropyrrolidine.",

abstract = "A simple and straightforward synthesis of diporphyrins and pentaporphyrins is reported here. The supramolecular interactions of the new porphyrin derivatives with C60 and PyC60 (a pyridyl [60]fulleropyrrolidine) were evaluated by absorption and fluorescence titrations in toluene. While no measurable modifications of the absorption and fluorescence spectra were observed upon addition of C60 to the porphyrin derivatives, the addition of PyC60 to the corresponding mono-Zn(II) porphyrins resulted in the formation of Zn(porphyrin)-PyC60 coordination complexes and the binding constants were calculated. Results show that the four free-base porphyrin units in pentaporphyrin 6 have a significant contribution in the stabilization of the 6-PyC60 complex. The crystal and molecular features of the pentaporphyrin Zn5 were unveiled using single-crystal X-ray diffraction studies.",

author = "Costa, {Joana I T} and Farinha, {Andreia S F} and Paz, {Filipe A Almeida} and Tom{\'e}, {Augusto C}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Thanks are due to the University of Aveiro and Funda{\c c}{\~a}o para a Ci{\^e}ncia e a Tecnologia (FCT, Portugal) for the financial support to the project PTDC/QEQ-QOR/6160/2014 and the research units UID/QUI/00062/2019 and UID/CTM/50011/2019 through national funds and where applicable co-financed by the FEDER, within the PT2020 Partnership Agreement, and also to the Portuguese NMR Network.",

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AU - Tomé, Augusto C

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Thanks are due to the University of Aveiro and Fundação para a Ciência e a Tecnologia (FCT, Portugal) for the financial support to the project PTDC/QEQ-QOR/6160/2014 and the research units UID/QUI/00062/2019 and UID/CTM/50011/2019 through national funds and where applicable co-financed by the FEDER, within the PT2020 Partnership Agreement, and also to the Portuguese NMR Network.

PY - 2019/9/1

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N2 - A simple and straightforward synthesis of diporphyrins and pentaporphyrins is reported here. The supramolecular interactions of the new porphyrin derivatives with C60 and PyC60 (a pyridyl [60]fulleropyrrolidine) were evaluated by absorption and fluorescence titrations in toluene. While no measurable modifications of the absorption and fluorescence spectra were observed upon addition of C60 to the porphyrin derivatives, the addition of PyC60 to the corresponding mono-Zn(II) porphyrins resulted in the formation of Zn(porphyrin)-PyC60 coordination complexes and the binding constants were calculated. Results show that the four free-base porphyrin units in pentaporphyrin 6 have a significant contribution in the stabilization of the 6-PyC60 complex. The crystal and molecular features of the pentaporphyrin Zn5 were unveiled using single-crystal X-ray diffraction studies.

AB - A simple and straightforward synthesis of diporphyrins and pentaporphyrins is reported here. The supramolecular interactions of the new porphyrin derivatives with C60 and PyC60 (a pyridyl [60]fulleropyrrolidine) were evaluated by absorption and fluorescence titrations in toluene. While no measurable modifications of the absorption and fluorescence spectra were observed upon addition of C60 to the porphyrin derivatives, the addition of PyC60 to the corresponding mono-Zn(II) porphyrins resulted in the formation of Zn(porphyrin)-PyC60 coordination complexes and the binding constants were calculated. Results show that the four free-base porphyrin units in pentaporphyrin 6 have a significant contribution in the stabilization of the 6-PyC60 complex. The crystal and molecular features of the pentaporphyrin Zn5 were unveiled using single-crystal X-ray diffraction studies.

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A Convenient Synthesis of Pentaporphyrins and Supramolecular Complexes with a Fulleropyrrolidine.

Abstract

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CCDC 1825479: Experimental Crystal Structure Determination : (mu-5,10,15,20-tetrakis(2,3,5,6-tetrafluoro-4-[4-(10,15,20-triphenylporphyrinato-5-yl)phenoxy]phenyl)porphyrinato)-pentakis(methanol)-penta-zinc unknown solvate

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A Convenient Synthesis of Pentaporphyrins and Supramolecular Complexes with a Fulleropyrrolidine.

Abstract

Bibliographical note

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Datasets

CCDC 1825479: Experimental Crystal Structure Determination : (mu-5,10,15,20-tetrakis(2,3,5,6-tetrafluoro-4-[4-(10,15,20-triphenylporphyrinato-5-yl)phenoxy]phenyl)porphyrinato)-pentakis(methanol)-penta-zinc unknown solvate

Cite this