Preparation and characterization of water soluble viologen-linked trisulfonatophenylporphyrin (TPPSC V)
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Viologen
Moiety
Methylene
Methylene blue
Viologen
Cucurbituril
Conjugate
Electron acceptor
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Viologen
Electrochromic devices
Biphenyl
Radical ion
Hydroquinone
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Journal of the Chemical Society Faraday Transactions 1 Physical Chemistry in Condensed Phases (1977)
The reactions of triplet and singlet methylene with cis- and trans-but-2-ene have been studied over the temperature range 350–473 K. The results yield a value of (36.5 ± 3.2) kJ mol–1 for the energy separation between singlet and triplet methylene, and provide further confirmation of the assumption that singlet methylene reactions with hydrocarbons proceed with activation energies close to zero. Previous evidence for the similar reactivities of triplet methylene and the methyl radical receives additional support.
Methylene
Ene reaction
Methylene blue
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Moiety
Methylene
Methylene blue
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The reactions of singlet and triplet methylene have been studied with 14C and tritium tracers. Triplet methylene is intercepted by O2, and oxidized to CO or CO2. In the absence of O2, triplet methylene reacts with 2-butene, and the excited biradical can decompose to methyl plus butenyl. In saturated systems, triplet methylene is very long-lived and undergoes radical-radical reactions. Singlet methylene reacts with ethylene while still vibrationally excited. Singlet 14CH2 can undergo isotopic exchange with CO to form 14CO; 1(14CH2) can also react by abstraction of Cl or Br from methyl halide.
Methylene
Singlet fission
Methylene blue
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A new porphyrin-containing host has an exceptionally high affinity for viologen guests, with binding constants as high as Kass = 7 × 106M–1 in organic solvents, allowing the construction of porphyrin–viologen rotaxanes.
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Viologen functionalized conducting polymers synthesized from the substituted monomers whon in the figure are interesting materials with possible applications in redox or electrocatalysis, sensors, and electrochromic devices. Monomers and polymers with various numbers of methylene groups separating the thiophene units and the redoxactive viologen moieties have been synthesized and characterized. magnified image
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Electrochromic devices
Methylene
Methylene blue
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Compounds containing a viologen linked to a porphyrin via a number (n= 4–7) of methylene groups have been synthesized and photoinduced long-range electron transfer between porphyrin and viologen was observed. The photoexcited singlet state of the porphyrin was quenched by the bonded viologen in viologen-linked porphyrins. The fluorescence decay profiles of the viologen-linked porphyrins consist of a sum of two first-order decays with shorter and longer lifetimes. The shorter lifetime arises from the direct quenching of the photoexcited singlet state of the porphyrin by the linked viologen. The intramolecular electron transfer process from the porphyrin to the bonded viologen becomes less effective when the methylene chain length becomes longer.
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Methylene
Photoinduced electron transfer
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Organic materials have gained considerable attention for electrochromic (EC) applications owing to improved EC performance and good processability. As a class of well-recognized organic EC materials, viologens have received persistent attention due to the structural versatility and property tunability, and are major active EC components for most of the marketed EC devices. Over the past two decades, extensive efforts have been made to design and synthesize different types of viologen-based materials with enhanced EC properties. This review summarizes chemical structures, preparation and EC properties of various latest viologen-based electrochromes, including small viologen derivatives, main-chain viologen-based polymers, conjugated polymers with viologen side-chains and viologen-based organic/inorganic composites. The performance enhancement mechanisms are concisely discussed. The current marketed viologens-based electrochromic devices (ECDs) are briefly introduced and an outlook on the challenges and future exploration directions for viologen-based materials and their ECDs are also proposed.
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Electrochromic devices
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