Synthesis and Spectroscopic and Electrochemical Properties of an Axially Symmetric Fullerene–Porphyrin Dyad with a Rigid Pyrrolo[3,4-<i>c</i>]pyrrole Spacer

Konev, Alexander S.; Khlebnikov, Alexander F.; Nikiforova, T. G.; Virtsev, Alexander A.; Frauendorf, Holm

doi:10.1021/jo302763a

Cited by 22 publications

(17 citation statements)

References 52 publications

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“…The prerequisite for a successful polymerization process is that the single step in the polymerization chain proceeds with a yield close to quantitative. In our previous study, we found that the reaction of aziridine 3 with maleimide 4 in chlorobenzene under microwave irradiation (45 min, 160 W, maximum temperature reached: 126 °C) gives the expected trans ‐cycloadduct 5 as sole diastereomer in 95% yield (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

The Implication of 1,3‐Dipolar Cycloaddition of Azomethine Ylides to the Synthesis of Main‐Chain Porphyrin Oligomers

Konev

Lukyanov

Vlasov

et al. 2014

Macro Chemistry & Physics

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The polycycloaddition of azomethine ylides to dipolarophiles is described for the first time. Use of (cis,cis)‐bis‐aziridines as a source of azomethine ylides allows selective polyaddition to be realized, which leads to oligomers exclusively with trans‐substituted pyrrolidine rings and modest molecular weights (ca. 5–10 kDa). The fluorescent, electrochemical, electrochromic, and non‐linear optical properties of the main‐chain free‐base porphyrin oligomer, synthesized by the developed procedure, are studied. An enhancement of the optical power limiting effect in a porphyrin oligomer solution is registered against that of the monomer.

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Section: Resultsmentioning

confidence: 99%

The Implication of 1,3‐Dipolar Cycloaddition of Azomethine Ylides to the Synthesis of Main‐Chain Porphyrin Oligomers

Konev

Lukyanov

Vlasov

et al. 2014

Macro Chemistry & Physics

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“…Figure 2s hows ac omparison of UV/Vis spectra of PDI-SiPc (4) and PDI-SiPc-C 60 (1)w itht hose of reference compounds di(pmethylbenzoate)silicont etra-tert-butylphthalocyanine (SiPc-ref; Scheme4)a nd a1 :1 mixture of N,N-di(2'-ethylhexyl) 6,7,4:9, and SiPc-refa ss olutions in benzonitrile.T he reference compounds show typical absorption spectral behaviorf or Pc, C 60 -ref, and PDI. Thus, the spectrumo fP DI-ref features two main absorption bands, with maxima at 489 and 523 nm, andt hat of SiPcref features intense Soret and Q-bands at 363 and 693 nm, respectively.A ll of these bands are common to the absorption spectra of both PDI-SiPc (4)a nd PDI-SiPc-C 60 (1), and the only minor variations in wavelengths indicate an absence of significant electronic interactions betweent he chromophores in the ground state.…”

Section: Opticaland Redox Propertiesmentioning

confidence: 99%

“…Multichromophoric systems that undergo photoinduced electron-and/or energy-transfer processes are of great interest as model photosynthetic systems, [1][2][3][4][5][6][7][8][9][10][11][12] and are potentially useful as active materials in organic photovoltaics (OPV). [1][2][3][4] The use of different buildingb locks, each of which performs ac ertain function, has led to sophisticateds ystemst hat, after excitation of antenna-type subunits,a fford long-lived charge-separated states (CSSs) following as equential mechanism of energy transfer followedby electron transfer.…”

Section: Introductionmentioning

confidence: 99%

Multichromophoric Perylenediimide–Silicon Phthalocyanine–C₆₀ System as an Artificial Photosynthetic Analogue

Martín‐Gomis

Thomas

Fernández‐Lázaro

et al. 2017

Chemistry A European J

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Sequential photoinduced energy transfer followed by electron transfer and the formation of charge-separated states, which are primary events of natural photosynthesis, have been demonstrated in a newly synthesized multichromophoric covalently linked triad, PDI-SiPc-C . The triad comprises a perylenediimide (PDI), which primarily fulfils antenna and electron-acceptor functionalities, silicon phthalocyanine (SiPc) as an electron donor, and fulleropyrrolidine (C ) as a second electron acceptor. The multi-step convergent synthetic procedure developed here produced good yields of the triad and control dyads, PDI-SiPc and SiPc-C . The structures and geometries of the newly synthesized donor-acceptor systems have been established from spectral, computational, and electrochemical studies with reference to appropriate control compounds. Ultrafast energy transfer from PDI* to SiPc in the case of PDI-SiPc and PDI-SiPc-C was witnessed. An energy-level diagram established from spectral and electrochemical data suggested the formation of two types of charge-separated states, that is, PDI-SiPc -C and PDI -SiPc -C from the SiPc* in the triad, with generation of the latter being energetically more favorable. However, photochemical studies involving femtosecond transient spectroscopy revealed the formation of PDI-SiPc -C as a major charge-separated product. This observation may be rationalized in terms of the closer spatial proximity to SiPc of C compared to PDI in the triad. The charge-separated state persisted for a few nanoseconds prior to populating the SiPc* state during charge recombination.

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“…1, 2 ,3 ,4-6 These systems are often composed of C 60 conjugated to planar aromatics to generate molecules in which individual characteristics of the components are often modulated, to give rise to new properties. [8][9][10][11][12][13] It is important to note that one of the highest power conversion efficiencies (PCE) in solutionprocessed organic photovoltaic cells is based on the polymer blends with fullerene derivative as the acceptor component. Importantly, different synthetic strategies have been developed for accessing architectures like C 60 -donor (AD), C 60 -acceptor (AA) or C 60 -donor-C 60 (ADA).…”

Section: Introductionmentioning

confidence: 99%

Fulleropyrrolidine molecular dumbbells act as multi-electron-acceptor triads. Spectroscopic, electrochemical, computational and morphological characterizations

et al. 2015

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a We synthesized three dumbbell-like compounds 2a-c, each containing two C60 groups at the periphery and pyromellitic diimide (PMDI) in the middle, and examined their electronic as well as assembly characteristics with both experimental and computational methods. Cyclic voltammetry (CV) measurements revealed that each of three electron-accepting (AAA) triads could accommodate up to eight electrons. Computational studies (density functional theory, DFT) of 2a-c at PBEPBE/6-311G(d,p) level of theory, with B3LYP/6-31G(d) optimized geometries, revealed that HOMO-LUMO energy gaps are similar to those of the model compound [6,6]-phenyl-C61-butyric acid methyl ester (PCBM). Compounds 2a-c were also found to assemble into vesicles and nanoparticles on the copper grid (100-300 nm, TEM), while giving more sizeable aggregates after a deposition on the glass (SEM, > 5 µm). Understanding the packing of 2a-c on various solid substrates, as well as the assembly characteristics in general, is important for tuning the properties and fabrication of electronic/optical devices. On the basis of the results of conformational analysis (MM and DFT calculations), we deduced that different alkyl spacers in 2a-c ought to play a role in π-π interactions between the aromatic components of the triad to guide the packing and therefore morphology of the material.Three novel fulleropyrrolidine dumbbells consisting three electron acceptor moieties joined by alkyl linker displaying tunable electrical and morphological properties were synthesized and characterized.

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Synthesis and Spectroscopic and Electrochemical Properties of an Axially Symmetric Fullerene–Porphyrin Dyad with a Rigid Pyrrolo[3,4-c]pyrrole Spacer

Cited by 22 publications

References 52 publications

The Implication of 1,3‐Dipolar Cycloaddition of Azomethine Ylides to the Synthesis of Main‐Chain Porphyrin Oligomers

The Implication of 1,3‐Dipolar Cycloaddition of Azomethine Ylides to the Synthesis of Main‐Chain Porphyrin Oligomers

Multichromophoric Perylenediimide–Silicon Phthalocyanine–C₆₀ System as an Artificial Photosynthetic Analogue

Fulleropyrrolidine molecular dumbbells act as multi-electron-acceptor triads. Spectroscopic, electrochemical, computational and morphological characterizations

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Synthesis and Spectroscopic and Electrochemical Properties of an Axially Symmetric Fullerene–Porphyrin Dyad with a Rigid Pyrrolo[3,4-c]pyrrole Spacer

Cited by 22 publications

References 52 publications

The Implication of 1,3‐Dipolar Cycloaddition of Azomethine Ylides to the Synthesis of Main‐Chain Porphyrin Oligomers

The Implication of 1,3‐Dipolar Cycloaddition of Azomethine Ylides to the Synthesis of Main‐Chain Porphyrin Oligomers

Multichromophoric Perylenediimide–Silicon Phthalocyanine–C60 System as an Artificial Photosynthetic Analogue

Fulleropyrrolidine molecular dumbbells act as multi-electron-acceptor triads. Spectroscopic, electrochemical, computational and morphological characterizations

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Multichromophoric Perylenediimide–Silicon Phthalocyanine–C₆₀ System as an Artificial Photosynthetic Analogue