Syntheses and Photophysical Properties of Fulleropyrrolidines Containing Photoactive Units

Wei, Xian‐Wen; Yao, Side; Yin, Geping; Suo, Zhiyong; Xu, Zheng; Wang, Pei; Zhang, Weijun; Chen, Ping; Zhang, Yun; Li, Chongde; Yin, Ning

doi:10.1081/fst-120005442

Cited by 9 publications

(5 citation statements)

References 39 publications

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“…Although the emission quantum yields are small, we first note that the emission quantum yield of the simple fulleropyrollidine 7 is increased by a factor of ca. 4 relative to that of C 60 . This increase is most likely due to the breaking of symmetry in the C 60 .…”

Section: Resultsmentioning

confidence: 98%

Fulleropyrrolidine End-Capped Molecular Wires for Molecular Electronics—Synthesis, Spectroscopic, Electrochemical, and Theoretical Characterization

et al. 2010

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In continuation of previous studies showing promising metal-molecule contact properties a variety of C(60) end-capped "molecular wires" for molecular electronics were prepared by variants of the Prato 1,3-dipolar cycloaddition reaction. Either benzene or fluorene was chosen as the central wire, and synthetic protocols for derivatives terminated with one or two fullero[c]pyrrolidine "electrode anchoring" groups were developed. An aryl-substituted aziridine could in some cases be employed directly as the azomethine ylide precursor for the Prato reaction without the need of having an electron-withdrawing ester group present. The effect of extending the π-system of the central wire from 1,4-phenylenediamine to 2,7-fluorenediamine was investigated by absorption, fluorescence, and electrochemical methods. The central wire and the C(60) end-groups were found not to electronically communicate in the ground state. However, the fluorescence of C(60) was quenched by charge transfer from the wire to C(60). Quantum chemical calculations predict and explain the collapse of coherent electronic transmission through one of the fulleropyrrolidine-terminated molecular wires.

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Section: Resultsmentioning

confidence: 98%

Fulleropyrrolidine End-Capped Molecular Wires for Molecular Electronics—Synthesis, Spectroscopic, Electrochemical, and Theoretical Characterization

et al. 2010

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“…All solvents were commercial and also used as received. ZnTCPP and C60PPy were synthesized according to literature reported methods 45 46 . NMR spectra were recorded on a Bruker AVANCE 500 MHz spectrometer.…”

Section: Methodsmentioning

confidence: 99%

Enhancement of p-Type Dye-Sensitized Solar Cell Performance by Supramolecular Assembly of Electron Donor and Acceptor

Tian

Oscarsson

Gabrielsson

et al. 2014

Sci Rep

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Supramolecular interactions based on porphyrin and fullerene derivatives were successfully adopted to improve the photovoltaic performance of p-type dye-sensitized solar cells (DSCs). Photoelectron spectroscopy (PES) measurements suggest a change in binding configuration of ZnTCPP after co-sensitization with C60PPy, which could be ascribed to supramolecular interaction between ZnTCPP and C60PPy. The performance of the ZnTCPP/C60PPy-based p-type DSC has been increased by a factor of 4 in comparison with the DSC with the ZnTCPP alone. At 560 nm, the IPCE value of DSCs based on ZnTCPP/ C60PPy was a factor of 10 greater than that generated by ZnTCPP-based DSCs. The influence of different electrolytes on charge extraction and electron lifetime was investigated and showed that the enhanced V oc from the Co 21/31 (dtbp) 3 -based device is due to the positive E F shift of NiO. P-type dye-sensitized solar cells (DSCs) 1-10 have attracted intensive interest in the community due to the potential applications in tandem devices 11,12 with n-type DSCs 13 as well as in the artificial photosynthesis systems 14,15 . So far, the highest efficiency of p-type dye-sensitized solar cells is 1.3% obtained by the combination between an organic dye and a cobalt redox couple 16 . In DSCs, the photosensitizer is always one of the crucial components of the devices. To date, some organic as well as inorganic photosensitizers have been developed for p-type DSCs [2][3][4][5]12,[17][18][19][20][21] . In order to improve the photovoltaic properties of p-type DSCs, the recombination process between injected holes in the valence band (VB) of the p-type semiconductor and reduced photosensitizer should be inhibited as much as possible 4 . This problem can be addressed by judicious design of the photosensitizer, including extension of the conjugated system to increase the distance between the electron acceptor unit and the p-type semiconductor surface. This synthetic approach has been shown to provide a longer lifetime of the charge separated state 12,22 . Recently, a porphyrin dye showed a promising device efficiency up to 11%, a comparable efficiency to classic Ru photosensitizers that are ubiquitous in n-type DSC 23. These two points were the main motivations for using porphyrin dyes in p-type DSCs. Lindquist and co-workers adopted the mesotetra(carboxyphenyl) porphyrin (TCPP) for p-type DSCs in 1999 24 . However, at that moment the efficiency of the p-type DSCs based on this porphyrin dye was very unsatisfying, around 0.003%, with the highest incident photon-to-current conversion efficiency (IPCE) value of 0.24% at 540 nm. The poor photovoltaic properties were probably due to the fast hole recombination processes and the quality of the NiO films. Inspired by previous examples of supramolecular interaction between porphyrin and C60 and the fast charge transfer process from porphyrin to C60 derivatives [25][26][27][28][29] , a C60 derivative, N-methyl-2-(49-pyridyl)-3,4-fulleropyrrolidine (C60PPy) was adopted to carry out the formation of the supr...

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“…Chemicals were purchased from Aldrich Chemical Co., Acros Organics, or Fluka Chemie and used as received without further purification. The C 60 derivative 8 was synthesized, accordingly with the literature, by a Prato reaction of C 60 with benzaldehyde in the presence of sarcosine . The monitoring of the reactions was carried out by thin-layer chromatography (TLC), employing aluminum sheets precoated with silica gel 60 F 254 (Merck).…”

Section: Methodsmentioning

confidence: 99%

Stabilization of Charge-Separated States in Phthalocyanine−Fullerene Ensembles through Supramolecular Donor−Acceptor Interactions

et al. 2006

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A novel ZnPc-C60 dyad (3), in which two photoactive units are brought together by a phenylenevinylene spacer has been synthesized. The synthetic strategy en route toward 3 involves a Heck reaction to attach 4-vinylbenzaldehyde to a monoiodophthalocyanine precursor, followed by standard cycloaddition of azomethine ylides (generated from the formylPc derivative and N-methylglycine) to one of the double bonds of C60. Electrochemical studies reveal that in 3 the ZnPc is about 39 mV more difficult to oxidize than in the corresponding ZnPc reference, which points to appreciable electronic communication between ZnPc and C60 in the ground state. In the excited state, photoexcitation leads to the formation of a charge-separated ZnPc*+-C60*- state, for which a lifetime of 130 ns was determined in THF. Hetero-association between complementary Pcs (1 and 2 or 3 and 2), which carry different peripheral functionalities (i.e., either electron-donating alkoxy groups or electron-deficient alkylsulfonyl chains) was assessed by different techniques. They provided evidence for donor-acceptor 1:1 complex formation with a stability constant of ca. 10(5) M(-1) in CHCl3. Interestingly, hetero-association of ZnPc-C60 dyad 3 with an electron-deficient PdPc (2) allowed the construction of supramolecular triads, in which a substantial stabilization of the radical pair is seen relative to that of the covalently linked dyad ZnPc-C60 (3).

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Syntheses and Photophysical Properties of Fulleropyrrolidines Containing Photoactive Units

Cited by 9 publications

References 39 publications

Fulleropyrrolidine End-Capped Molecular Wires for Molecular Electronics—Synthesis, Spectroscopic, Electrochemical, and Theoretical Characterization

Fulleropyrrolidine End-Capped Molecular Wires for Molecular Electronics—Synthesis, Spectroscopic, Electrochemical, and Theoretical Characterization

Enhancement of p-Type Dye-Sensitized Solar Cell Performance by Supramolecular Assembly of Electron Donor and Acceptor

Stabilization of Charge-Separated States in Phthalocyanine−Fullerene Ensembles through Supramolecular Donor−Acceptor Interactions

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