Electron Transfer Rates in an Adsorbed C<sub>60</sub>‐Porphyrin Dyad

Fortgang, Philippe; Urbani, Maxence; Holler, Michel; Nierengarten, Jean‐François; Moreau, Alain; Delavaux‐Nicot, Béatrice; Maisonhaute, Emmanuel

doi:10.1002/elan.201400618

Electroanalysis

2015

DOI: 10.1002/elan.201400618

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Electron Transfer Rates in an Adsorbed C₆₀‐Porphyrin Dyad

Philippe Fortgang¹,

Maxence Urbani²,

Michel Holler³

et al.

Abstract: Association of C60 and porphyrin entities to build light harvesting systems is a promising alternative for future photovoltaic devices. Herein, we determine the electron transfer rates in a C60‐porphyrin dyad anchored onto a gold ultramicroelectrode via the porphyrin core. Similar rates are observed for both redox entities, suggesting a tilt of the molecules allowing an efficient through‐space communication between C60 and the electrode.

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Cited by 3 publications

References 58 publications

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Coordination‐Driven Folding in Multi‐Zn^II‐Porphyrin Arrays Constructed on a Pillar[5]arene Scaffold

Trinh

Nierengarten

Aziza

et al. 2017

Chemistry A European J

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Pillar[5]arene derivatives bearing peripheral porphyrin subunits have been efficiently prepared from a deca-azide pillar[5]arene building block (17) and Zn -porphyrin derivatives bearing a terminal alkyne function (9 and 16). For the resulting deca-Zn -porphyrin arrays (18 and 20), variable temperature NMR studies revealed an intramolecular complexation of the peripheral Zn -porphyrin moieties by 1,2,3-triazole subunits. As a result, the molecules adopt a folded conformation. This was further confirmed by UV/Vis spectroscopy and cyclic voltammetry. In addition, we have also demonstrated that the coordination-driven unfolding of 18 and 20 can be controlled by an external chemical stimulus. Specifically, addition of an imidazole derivative (22) to solution of 18 or 20 breaks the intramolecular coordination at the origin of the folding. The resulting molecular motions triggered by the addition of the imidazole ligand mimic the blooming of a flower.

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Coordination‐Driven Folding in Multi‐Zn^II‐Porphyrin Arrays Constructed on a Pillar[5]arene Scaffold

Trinh

Nierengarten

Aziza

et al. 2017

Chemistry A European J

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A Rotaxane Scaffold for the Construction of Multiporphyrinic Light‐Harvesting Devices

Delavaux‐Nicot

Aziza

Nierengarten

et al. 2017

Chemistry A European J

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As ophisticated photoactive molecular device has been prepared by combiningr ecent conceptsf or the preparation of multifunctional nanomolecules (click chemistry on multifunctional scaffolds) with supramolecular chemistry (self-assembly to prepare rotaxanes). Specifically,aclickable [2]rotaxane scaffold incorporating af ree-base porphyrin stopperh as been prepared and functionalized with ten peripheralZ n(II)-porphyrinm oieties. Electrochemical investigations of the final compound revealed ap eculiar behavior resultingf rom the intramolecular coordinationo ft he Zn(II) porphyrin moieties to 1,2,3-triazoleu nits. Finally,s teady state investigationso ft he compound combining Zn(II) and free-base porphyrin moieties have shown that this compoundi salight-harvesting device capable of channeling the light energy from the peripheralZ n(II)-porphyrins ubunits to the core by singlet-singlet energy transfer.

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Clicked BODIPY‐Fullerene‐Peptide Assemblies: Studies of Electron Transfer Processes in Self‐Assembled Monolayers on Gold Surfaces

Rabah,

Nasrallah,

Wright

et al. 2024

ChemPlusChem

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Two BODIPY‐C60‐peptide assemblies were synthesized by CuAAC reactions of BODIPY‐C60 dyads and a helical peptide functionalized with a terminal alkyne group and an azide group, respectively. The helical peptide within these assemblies was functionalized at its other end by a disulfide group, allowing formation of self‐assembled monolayers (SAMs) on gold surfaces. Characterizations of these SAMs, as well as those of reference molecules (BODIPY‐C60‐alkyl, C60‐peptide and BODIPY‐peptide), were carried out by PM‐IRRAS and cyclic voltammetry. BODIPY‐C60‐peptide SAMs are more densely packed than BODIPY‐C60‐alkyl and BODIPY‐peptide based SAMs. These findings were attributed to the rigid peptide helical conformation along with peptide‐peptide and C60‐C60 interactions within the monolayers. However, less dense monolayers were obtained with the target assemblies compared to the C60‐peptide, as the BODIPY entity likely disrupts organization within the monolayers. Finally, electron transfer kinetics measurements by ultra‐fast electrochemistry experiments demonstrated that the helical peptide is a better electron mediator in comparison to alkyl chains. This property was exploited along with those of the BODIPY‐C60 dyads in a photo‐current generation experiment by converting the resulting excited and/or charge separated states from photo‐illumination of the dyad into electrical energy.

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Electron Transfer Rates in an Adsorbed C₆₀‐Porphyrin Dyad

Cited by 3 publications

References 58 publications

Coordination‐Driven Folding in Multi‐Zn^II‐Porphyrin Arrays Constructed on a Pillar[5]arene Scaffold

Coordination‐Driven Folding in Multi‐Zn^II‐Porphyrin Arrays Constructed on a Pillar[5]arene Scaffold

A Rotaxane Scaffold for the Construction of Multiporphyrinic Light‐Harvesting Devices

Clicked BODIPY‐Fullerene‐Peptide Assemblies: Studies of Electron Transfer Processes in Self‐Assembled Monolayers on Gold Surfaces

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Electron Transfer Rates in an Adsorbed C60‐Porphyrin Dyad

Cited by 3 publications

References 58 publications

Coordination‐Driven Folding in Multi‐ZnII‐Porphyrin Arrays Constructed on a Pillar[5]arene Scaffold

Coordination‐Driven Folding in Multi‐ZnII‐Porphyrin Arrays Constructed on a Pillar[5]arene Scaffold

A Rotaxane Scaffold for the Construction of Multiporphyrinic Light‐Harvesting Devices

Clicked BODIPY‐Fullerene‐Peptide Assemblies: Studies of Electron Transfer Processes in Self‐Assembled Monolayers on Gold Surfaces

Contact Info

Product

Resources

About

Electron Transfer Rates in an Adsorbed C₆₀‐Porphyrin Dyad

Coordination‐Driven Folding in Multi‐Zn^II‐Porphyrin Arrays Constructed on a Pillar[5]arene Scaffold

Coordination‐Driven Folding in Multi‐Zn^II‐Porphyrin Arrays Constructed on a Pillar[5]arene Scaffold