Photoinduced Electron Transfer between a Self-Assembled Resorcinarene−[60]Fullerene Complex and Poly(3-hexylthiophene) in Langmuir−Blodgett Films

Vuorimaa, Elina; Vuorinen, Tommi; Tkachenko, Nikolai V.; Cramariuc, Oana; Hukka, Terttu I.; Nummelin, Sami; Shivanyuk, Alexander; Lemmetyinen, Helge

doi:10.1021/la010786u

Cited by 20 publications

(19 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…C 60 has been noncovalently attached to SAMs [158,179]. In one instance, a crown ether-functionalized C 60 was incorporated into a SAM by the interactions between the crown ether and ammonium groups on a modified electrode [158].…”

Section: Redox Species Used For Electrochemical Determination Of Kmentioning

confidence: 99%

“…In one instance, a crown ether-functionalized C 60 was incorporated into a SAM by the interactions between the crown ether and ammonium groups on a modified electrode [158]. The resorcinarene molecule has been used as a recognition element to incorporate unsubstituted C 60 molecules to SAMs [179]. The majority of the electron transfer studies involving C 60 have used spectroscopic techniques [15,164,180–182].…”

Section: Redox Species Used For Electrochemical Determination Of Kmentioning

confidence: 99%

See 1 more Smart Citation

Electrochemistry of redox-active self-assembled monolayers

Eckermann

Feld

Shaw

et al. 2010

Coordination Chemistry Reviews

530

492

View full text Add to dashboard Cite

Redox-active self-assembled monolayers (SAMs) provide an excellent platform for investigating electron transfer kinetics. Using a well-defined bridge, a redox center can be positioned at a fixed distance from the electrode and electron transfer kinetics probed using a variety of electrochemical techniques. Cyclic voltammetry, AC voltammetry, electrochemical impedance spectroscopy, and chronoamperometry are most commonly used to determine the rate of electron transfer of redoxactivated SAMs. A variety of redox species have been attached to SAMs, and include transition metal complexes (e.g., ferrocene, ruthenium pentaammine, osmium bisbipyridine, metal clusters) and organic molecules (e.g., galvinol, C 60 ). SAMs offer an ideal environment to study the outer-sphere interactions of redox species. The composition and integrity of the monolayer and the electrode material influence the electron transfer kinetics and can be investigated using electrochemical methods. Theoretical models have been developed for investigating SAM structure. This review discusses methods and monolayer compositions for electrochemical measurements of redox-active SAMs.

show abstract

Section: Redox Species Used For Electrochemical Determination Of Kmentioning

confidence: 99%

Section: Redox Species Used For Electrochemical Determination Of Kmentioning

confidence: 99%

Electrochemistry of redox-active self-assembled monolayers

Eckermann

Feld

Shaw

et al. 2010

Coordination Chemistry Reviews

530

492

View full text Add to dashboard Cite

show abstract

“…41,43,47,50,[55][56][57][58] The method is based on measurements of the Maxwell displacement charge by placing the molecular layer into a flat capacitor. 59,60 The molecular film layer or layers are deposited upon a semitransparent electrode, such as indium tin oxide (ITO), and covered by a top electrode, which can be a drop of a liquid metal, e.g.…”

Section: Photovoltage Studies Of Electron Transfer In Single D-a Pairmentioning

confidence: 99%

“…40,41,43,50,[56][57][58] Although the phytochlorin-fullerene dyad, PhF (Fig. 3), is not at a glance an idealistic D-A molecule for LB film formation, it forms, being mixed with ODA at concentrations of 50 mol% and lower, stable monolayers, which can be transferred onto a solid substrate.…”

Section: Photovoltage Studies Of Electron Transfer In Single D-a Pairmentioning

confidence: 99%

Photoinduced intra- and intermolecular electron transfer in solutions and in solid organized molecular assemblies

Lemmetyinen

Tkachenko

Efimov

et al. 2011

Phys. Chem. Chem. Phys.

View full text Add to dashboard Cite

The present paper highlights results of a systematic study of photoinduced electron transfer, where the fundamental aspects of the photochemistry occurring in solutions and in artificially or self-assembled molecular systems are combined and compared. In photochemical electron transfer (ET) reactions in solutions the electron donor, D, and acceptor, A, have to be or to diffuse to a short distance, which requires a high concentration of quencher molecules and/or long lifetimes of the excited donor or acceptor, which cannot always be arranged. The problem can partly be avoided by linking the donor and acceptor moieties covalently by a single bond, molecular chain or chains, or rigid bridge, forming D-A dyads. The covalent combination of porphyrin or phthalocyanine donors with an efficient electron acceptor, e.g. fullerene, has a two-fold effect on the electron transfer properties. Firstly, the electronic systems of the D-A pair result in a formation of an exciplex intermediate upon excitation both in solutions and in solid phases. The formation of the exciplex accelerates the ET rate, which was found to be as fast as >10(12) s(-1). Secondly, the total reorganization energy can be as small as 0.3 eV, even in polar solvents, which allows nanosecond lifetimes for the charge separated (CS) state. Molecular assemblies can form solid heterogeneous, but organized systems, e.g. molecular layers. This results in more complex charge separation and recombination dynamics. A distinct feature of the ET in organized assemblies is intermolecular interactions, which open a possibility for a charge migration both in the acceptor and in the donor layers, after the primary intramolecular exciplex formation and charge separation in the D-A dyad. The intramolecular ET is fast (35 ps) and efficient, but the formed interlayer CS states have lifetimes in microsecond or even second time domain. This is an important result considering possible applications.

show abstract

“…[16] There have been several efforts to fabricate porphyrinfullerene systems by the LB technique, in an effort to prepare highly ordered multilayer films and therefore achieve efficient photo-to-current conversion properties. Recent examples of double linked porphyrin-fullerene dyads [17,18] and porphyrin-fullerene self-assemblies [19][20][21][22] are based on covalent bonds and electrostatic/metal-ligand axial coordination interactions of the functionalized fullerene to porphyrins, respectively. Formation of stable, uniform, and highly ordered LB films can result from the prevention of aggregation, which is the sever tendency of fullerenes, [23] by attaching a hydrophilic group and/or regulating filmforming conditions.…”

mentioning

confidence: 99%

Effect of Fullerene on Photocurrent Performance of 6‐O‐Porphyrin‐2,3‐di‐O‐stearoylcellulose Langmuir‐Blodgett Films

Sakakibara

Nakatsubo

2008

Macro Chemistry & Physics

View full text Add to dashboard Cite

Thin films consisting of 6‐O‐porphyrin‐2,3‐di‐O‐stearoylcellulose (H2PCS) and fullerene (C60) were fabricated for anodic photocurrent generation systems by the Langmuir‐Blodgett (LB) technique. The π‐complexation between the porphyrin moiety and C60 in the LB films was investigated by means of the surface pressure (π)‐area (A) isotherms, UV‐vis, and fluorescence spectroscopy. The photocurrent density generated from the H2PCS–C60 LB monolayer films exhibited an increase with increasing the C60 proportion and reached a maximum at a mixing ratio of 1:2, yielding a quantum yield of 12.5% and an IPCE (incident photon‐to‐current efficiency) of 0.50% at a bias potential of +100 mV vs. SCE. Furthermore, the LB five‐layer films could give rise to the IPCE value of 1.5% at +100 mV without significant decline of the quantum yields, which was due to the function of C60 as an electron carrier to improve the interlayer electron transfer through each layer. These results have demonstrated a promising method for preparing the donor–acceptor systems using cellulose as a scaffold in the LB films.magnified image

show abstract

Photoinduced Electron Transfer between a Self-Assembled Resorcinarene−[60]Fullerene Complex and Poly(3-hexylthiophene) in Langmuir−Blodgett Films

Cited by 20 publications

References 34 publications

Electrochemistry of redox-active self-assembled monolayers

Electrochemistry of redox-active self-assembled monolayers

Photoinduced intra- and intermolecular electron transfer in solutions and in solid organized molecular assemblies

Effect of Fullerene on Photocurrent Performance of 6‐O‐Porphyrin‐2,3‐di‐O‐stearoylcellulose Langmuir‐Blodgett Films

Contact Info

Product

Resources

About