Jean‐Paul Collin

Centre National de la Recherche Scientifique

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Jean‐Pierre Sauvage

Université de Strasbourg

106

Lucia Flamigni

Institute of Organic Synthesis and Photoreactivity

Valérie Heitz

Institut de Chimie de Strasbourg

Francesco Barigelletti

Institute of Organic Synthesis and Photoreactivity

Marc Beley

Université de Lorraine

Isabelle M. Dixon

Laboratoire de Chimie et Physique Quantiques

Jean‐Pierre Sauvage

Institut de Science et d'Ingénierie Supramoléculaires

Nicola Armaroli

Institute of Organic Synthesis and Photoreactivity

Etienne Baranoff

University of Birmingham

Barbara Ventura

Institute of Organic Synthesis and Photoreactivity

Cooperative Institutions

Centre National de la Recherche Scientifique

131

Institut de Chimie

Laboratoire de Chimie

Université de Strasbourg

Institut de Chimie de Strasbourg

Laboratoire de Chimie de Coordination

Sorbonne Université

École Polytechnique Fédérale de Lausanne

Max Planck Institute for Solid State Research

École Polytechnique

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Light-Driven Expulsion of the Sterically Hindering Ligand L in Tris-diimine Ruthenium(II) Complexes of the Ru(phen)₂(L)²⁺ Family: A Pronounced Ring Effect

Inorganic Chemistry (2005)

Jean‐Paul Collin Damien Jouvenot Masatoshi Koizumi Jean‐Pierre Sauvage

Three new ruthenium(II) complexes have been prepared which contain two 1,10-phenanthroline units and a third sterically hindering chelate. In one case, the hindering ligand is a disubstituted 2,2'-bipyridine (bpy) attached to two very bulky manisyl groups. The two other systems are similar in terms of size of the hindering groups (anisyl substituents) located close to the central metal. The complexes investigated in the Present Report are aimed at providing building blocks of future light-driven molecular machines. The photochemical expulsion of the sterically hindering chelate has thus been studied by UV−vis spectroscopy and 1H NMR. Surprisingly, the manisyl-containing complex turned out to be photochemically inert, indicating that a too bulky group acts as a protecting function versus decomplexation rather than as a destabilizing group. For the two other systems, a pronounced ring effect was observed: whereas the acyclic systems undergo fast photochemical expulsion of the bipy-based ligand, in the cyclic complex, the bipy-incorporating ring is decoordinated about 5 times less efficiently than the acyclic ligand of the previous case. These observations on the strong dependence of the photochemical behavior of the ruthenium(II) complexes on their structural properties are corroborated by X-ray diffraction studies on the three compounds investigated.

Diimine

10.1021/ic050246a

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Citations (53)

Metal‐Assembled Catenanes, Rotaxanes, and Knots

Nicola Armaroli Jean‐Claude Chambron Jean‐Paul Collin Christiane Dietrich‐Buchecker Lucia Flamigni

Catenane

Molecular machine

10.1002/9783527618248.ch45

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Citations (9)

Transition metal-assembled multiporphyrinic systems as models of photosynthetic reaction centre

Coordination Chemistry Reviews (1996)

Jean‐Paul Collin

Moiety

10.1016/0010-8545(95)01152-8

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Citations (49)

Switching of Electron- to Energy-Transfer by Selective Excitation of Different Chromophores in Arrays Based on Porphyrins and a Polypyridyl Iridium Complex

The Journal of Physical Chemistry B (2002)

Lucia Flamigni Giancarlo Marconi Isabelle M. Dixon Jean‐Paul Collin Jean‐Pierre Sauvage

Excitation at 350−355 nm of the dyads PAu−Ir, PH2−Ir and of the triads PH2−Ir−PAu and PZn−Ir−PAu where Ir, iridium(III) bis-terpyridine, is covalently linked to gold (III), free-base and zinc(II) tetraaryl-porphyrins (PAu, PH2, PZn), produces to a predominant extent the ligand centered triplet excited state of the iridium complex unit, 3Ir. The processes occurring in the arrays upon UV excitation have been characterized by steady state and time-resolved spectroscopic methods. Energy transfer to the porphyrin triplets dominates the deactivation of 3Ir in PAu−Ir, PH2−Ir, and PH2−Ir−PAu, with rates of 2.9 × 1010 s-1 (3Ir → 3PAu) and ca. 1011 s-1 (3Ir → 3PH2), in contrast to what has been shown to occur upon selective excitation of the PH2 unit, which yields electron transfer leading to charge separation. The different outcome is discussed on the basis of the overlap of the HOMO and LUMO orbitals involved in the electron-transfer reaction for the Ir acceptor unit and the PH2 donor unit, with the aid of semiempirical calculations. Remarkably, the PZn based array PZn−Ir−PAu displays efficient electron transfer with the formation of a charge separated state with unitary yield, irrespective of the component which is excited. A very high driving force, ΔG° = −1.1 eV, could explain the prevalence of the electron-transfer reaction in the latter case.

Chromophore

Electron acceptor

Acceptor

10.1021/jp025509q

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Citations (54)

Computational, Structural, and Mechanistic Analysis of the Electrochemically Driven Pirouetting Motion of a Copper Rotaxane

The Journal of Physical Chemistry B (2009)

Ganga Periyasamy Angélique Sour Jean‐Paul Collin Jean‐Pierre Sauvage F. Remacle

A mechanism for the electrochemically driven reorganization of a model copper [2]pseudorotaxane is proposed on the basis of density functional theory computations and validated by comparing to experimental results. We investigate in detail the ligand reorganization around the Cu ion from a 4 to 5 coordination number that follows the conversion of the oxidation state from +1 to +2. It is found that for both the oxidation and the reduction processes the rearrangement proceeds in a concerted fashion via a single transition state. Energy paths involving stable decoordinated-coordinated intermediates are computed to be higher in energy. The cyclic voltammogram simulated using the computed transition theory state rate constants in solvent medium is in good agreement with the experimental voltammogram. Further, we report on the computed concentration change of stable (Cu(+)(4), Cu(2+)(5)) and metastable species (Cu(2+)(4), Cu(+)(5)) during single cyclic voltammetry (CV) cycle as a function of the applied voltage or time (the subscripts 4 and 5 refer to the coordination number of the copper center).

Metastability

Rotaxane

10.1021/jp901214b

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Citations (20)

Copper-Complexed Pirouetting [2]pseudorotaxanes with Sulfur-Containing End-Groups Attached to the Thread: Synthesis, Electrochemical Studies, and Deposition on Gold Electrodes

Australian Journal of Chemistry (2009)

Jean‐Paul Collin Pierre Mobian Jean‐Pierre Sauvage Angélique Sour Yi‐Ming Yan

Two copper [2]pseudorotaxanes incorporating a macrocycle with two chelating sites (2,9-diphenyl-1,10-phenanthroline and 2,2′,6′,2″-terpyridine) and a thread based on crescent-shaped 2,2′-bipyridine derivatives have been synthesized and characterized. One of the threads was a hindering 2,2′-bipyridine functionalized by two thioctic-ended arms. The second thread was an 8,8′-diphenyl-3,3′-biisoquinoline functionalized by two thioether-ended arms. The electrochemical studies of the two copper [2]pseudorotaxanes, both in solution and anchored on a gold surface, showed only fast-moving systems in solution. The reasons of the inertness of the deposited complexes on gold electrode have been explored.

Thioether

Terpyridine

10.1071/ch09334

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Citations (6)

Energy Transfer in Rigid Ru(II)/Os(II) Dinuclear Complexes with Biscyclometalating Bridging Ligands Containing a Variable Number of Phenylene Units

Inorganic Chemistry (1996)

Francesco Barigelletti Lucia Flamigni Massimo Guardigli Alberto Juris Marc Beley

We have prepared rodlike cyclometalated Ru(II)/Os(II) dinuclear complexes, (ttp)Ru(dpb-(ph)(n)()-dpb)Os(ttp)(2+), where the biscyclometalating bridging ligands contain dipyridylbenzene fragments, dbp, separated by a variable number, n, of phenylene spacers, and the terminal ligand is a terpyridine derivative [dpbH is di-2-pyridyl-1,3-benzene, ttp is 4'-p-tolyl-2,2':6',2"-terpyridine, and n = 0-2]. The rigid bridging ligands keep the metal centers at a distance r(MM) = 11, 15.5, and 20 Å, depending on n. Photoinduced energy transfer has been investigated by luminescence spectroscopy in nitrile solvents at room temperature and at 77 K (i.e., in frozen medium). According to a classical description of the process, the energy transfer occurs in a nearly activationless regime, is governed by electronic factors, and can be described in terms of the Dexter-type mechanism. The obtained energy transfer rates roughly span 3 orders of magnitude and indicate (i) that the temperature (i.e., the state of the solvent) has a small influence on the process and (ii) that the interposed phenylene spacers are weak attenuators of intercenter electronic coupling, H [H = H(0) exp(-betar(MM)), with beta approximately 0.33 Å(-)(1)].

Terpyridine

Bridging ligand

Biphenylene

10.1021/ic9503085

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Citations (153)

Triplet−Triplet Energy Transfer between Porphyrins Linked via a Ruthenium(II) Bisterpyridine Complex

Inorganic Chemistry (1999)

Lucia Flamigni Francesco Barigelletti Nicola Armaroli Barbara Ventura Jean‐Paul Collin

The photophysical properties of a multicomponent array consisting of a free-base aryl-porphyrin and a gold(III) aryl-porphyrin, assembled via a central bis(terpyridine) ruthenium(II) complex, PH2−Ru−PAu, have been studied in low-temperature glassy media by steady state and time-resolved methods. Comparison of the photophysical properties of this triad with those of the reference molecular models and of the related dyads (Ru−PH2, Ru−PAu) allows the photoinduced processes occurring in PH2−Ru−PAu to be elucidated. The photoinduced processes in glassy media in the dyads Ru−PH2 and Ru−PAu are basically similar to those occurring at room temperature where the absorbed energy is transferred with 100% efficiency to the pertinent porphyrin lowest triplet state. For Ru-3PAu the decay to the ground state is similar to the model 3PAu and displays double-exponential behavior, while in the case of Ru−3PH2 some perturbing effect of the ruthenium center in accelerating the inter-system crossing to the ground state by the heavy atom effect can be noticed. In the triad PH2−Ru−PAu the primary photoinduced steps are similar to those occurring at room temperature and, by energy-transfer steps, populate both triplets of peripheral porphyrins. In contrast with room-temperature events, a further energy-transfer step from PH2−Ru−3PAu to the spatially opposed 3PH2−Ru−PAu (center to center distance = 2.1 nm) occurs in glassy media with a rate constant of 2.5 × 10 7 s-1, as probed by transient absorption spectroscopy. This process, which occurs by an exchange mechanism, is mediated by the interposed Ru(II) bisterpyridine complex, which acts as an electron relay.

Photoinduced electron transfer

Triad (sociology)

10.1021/ic980847k

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Citations (86)

CCDC 256429: Experimental Crystal Structure Determination

The Cambridge Structural Database (2005)

Jean‐Paul Collin J.‐C. Daran Olivier Jacquet E. Schulz Anton Trifonov

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Crystal (programming language)

10.5517/cc8ltxk

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A Triphenylamine/Bis(terpyridine)Ir^III Dyad for the Assembly of Charge‐Separation Constructs with Improved Performances

European Journal of Inorganic Chemistry (2007)

Lucia Flamigni Barbara Ventura Etienne Baranoff Jean‐Paul Collin Jean‐Pierre Sauvage

Abstract A new dyad DII‐Ir consisting of a triphenylamine donor and a bis(terpyridine)Ir III acceptor separated by a bridge composed of two benzamide groups has been synthesized. The electrochemical and photophysical properties of the dyad have been compared to those of a corresponding dyad D‐Ir characterized by a bridge connecting the donor and the acceptor consisting of a single benzamide unit. We show that, whereas the charge‐separation steps are still very efficient in the long dyad (≥99 %), charge recombination is slowed by a factor of three with respect to the short dyad. This encourages the use of this dyad in the assembly of a more elaborate array DII‐Ir‐A, expected to overcome the disappointingly low charge‐separation yield of a previously studied D‐Ir‐A short triad. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

Triphenylamine

Dyad

Terpyridine

Benzamide

Acceptor

Triad (sociology)

10.1002/ejic.200700669

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Citations (13)