Photochemical conversion and storage of solar energy by azobenzene.

Taoda, Hiroshi; Hayakawa, Kiyoshi; Kawase, Kaoru; Yamakita, Hiromi

doi:10.1252/jcej.20.265

Cited by 60 publications

(50 citation statements)

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“…19 The cis isomer is roughly 0.6 eV higher in energy than the trans form. (See Figure 1.) As an energy storage medium 20,8 this leads to a rather poor energy density, and, more importantly, the activation energy barrier of the cis→trans back reaction is low (<1 eV), corresponding to a half life of only a few hours for the metastable state. 20 No substitution pattern is known that significantly increases the activation barrier or the stored energy above that of unsubstituted AB, 21 making it unpractical in its isolated state for solar thermal fuel applications.…”

Section: Section: Energy Conversion and Storage; Energy And Charge Trmentioning

confidence: 99%

“…The cis isomer is found to be 0.58 eV higher in energy than the trans isomer, in good agreement with experimentally reported values. 20,22 For the cis→trans thermal back reaction, 23−25 we considered the inversion mechanism where one of the N atoms is inverted together with a perpendicular orientation of the N-phenyl ring, as shown in Figure 1. Our computed E a is 0.93 eV, which is also consistent with experimental data.…”

Section: Section: Energy Conversion and Storage; Energy And Charge Trmentioning

confidence: 99%

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Photoswitchable Molecular Rings for Solar-Thermal Energy Storage

Durgun

Grossman

2013

J. Phys. Chem. Lett.

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Solar-thermal fuels reversibly store solar energy in the chemical bonds of molecules by photoconversion, and can release this stored energy in the form of heat upon activation. Many conventional photoswichable molecules could be considered as solar thermal fuels, although they suffer from low energy density or short lifetime in the photoinduced high-energy metastable state, rendering their practical use unfeasible. We present a new approach to the design of chemistries for solar thermal fuel applications, wherein well-known photoswitchable molecules are connected by different linker agents to form molecular rings. This approach allows for a significant increase in both the amount of stored energy per molecule and the stability of the fuels. Our results suggest a range of possibilities for tuning the energy density and thermal stability as a function of the type of the photoswitchable molecule, the ring size, or the type of linkers. SECTION:Energy Conversion and Storage; Energy and Charge Transport E fficient utilization of the sun as a renewable and clean energy source is one of the greatest goals and challenges of this century due to the increasing demand for energy and its environmental impact. Numerous strategies exist to convert sunlight into useful forms of energy, including photocatalytic processes, artificial photosynthesis, 1,2 photothermal power plants, 3 and photovoltaic applications. 4 An alternative strategy to these is to convert and store the sun's energy directly in the chemical bonds of metastable photoisomers of suitable molecular systems. The stored energy can then be released as heat on demand by an external trigger. Ideally both the photisomerization and heat release reactions reversibly occur in a closed-cycle without changing the chemical composition. 5The clear advantage of such an approach is that the same material both converts and stores the sun's energy, providing a rechargeable fuel that can be safely transported and used ondemand; the materials used could, in principle, be cheap, nontoxic and abundant, and the cycle can be repeated thousands of times without any emission or waste.The idea of storing solar energy in chemical bonds was first introduced with the photoisomerization reactions of organic molecules (such as norbornadiene⇌quadricyclane 6,7 and the trans⇌cis isomers of azobenzene 8 ), although the concept was generally dismissed as unpractical 7 due to a number of reasons including degradation, instability of the photoinduced isomer (limited half-life or shelf life), low energy density, and cost. As such, the majority of recent experimental studies for such materials have focused on their photoswitchable properties, 9 as opposed to energy storage. The Ru-based organometallic complex (tetracarbonyl−diruthenium fulvalene) 10 has shown promise as a solar thermal fuel due to its high cyclability without degradation; however, substitutions for Ru must be found to reduce costs, and the volumetric energy density increased for practical applications. 11,12 Recently, a new s...

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Section: Section: Energy Conversion and Storage; Energy And Charge Trmentioning

confidence: 99%

Section: Section: Energy Conversion and Storage; Energy And Charge Trmentioning

confidence: 99%

Photoswitchable Molecular Rings for Solar-Thermal Energy Storage

Durgun

Grossman

2013

J. Phys. Chem. Lett.

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“…The mobility of benzyl chloride bonds in poly(4-chloromethylstyrene) (PMS) and related copolymers allows their reaction with various nucleophilic reagents. Also functionalized PCMS and related copolymers have been widely used in different processes such as bactericide polymers [3], photosensitizers [4], solar energy storage [5], photoresist [6], nonlinear optics [7], and prodrugs in biochemical application [8].…”

Section: -Chloromethylstyrene (Cms)mentioning

confidence: 99%

Modification of styrene polymer by attaching suitable groups as side chain

2009

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Chemical modification of inexpensive commercial polymers, such as styrene, is a safe methodology to obtain new copolymers. The 4-chloromethyl styrene (CMS) was copolymerized with styrene (in various mole ratios) by free radical polymerization method at 70 ºC using α,α-azobis(isobutyronitrile) (AIBN) as an initiator. The azide ion was covalently attached to the obtained copolymers with replacement of all the chlorine atoms in CMS units. The 1,3-dipolar click cycloaddition reaction between azido polymers and dimethyl acetylene dicarboxylate (DMAD) yielded polymers with 1,2,3-triazoles in side chain. The polymers, obtained in quantitative yields, were characterized by FT-IR and 1 H NMR spectroscopy; thermogravimetric analysis (TGA) and GPC studies. The thermogravimetric analysis (TGA) indicated that the thermal stability of copolymers increases with incorporation of 1,2,3-triazole groups in side chains of copolymers.

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“…Polystyrene (PS) and related co-polymers have been widely used in different processes, such as bactericide polymers [1], photo-sensitizers [2], solar energy storage [3], photo-resists [4], non-linear optics [5], cholesterol trapping of human serum [6] and prodrugs in biomedical applications [7].…”

Section: Introductionmentioning

confidence: 99%

“…Tris(trimethylsilyl)methyl, (Me 3 Si) 3 C, is referred to as trisyl and commonly denoted by 'Tsi'. Some polymers and co-polymers containing the very bulky Tsi groups were synthesized and their properties have been studied.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of new monomer and polymers of hindered silyl styrene

Assadi

Golipour

2007

Designed Monomers and Polymers

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Abstract-In this paper we report the synthesis of a new hindered organosilicon derivative of styrene monomer, homo-polymer and co-polymers. This new monomer was synthesized from reaction of the lithiated derivative of para-methyl styrene with tris(trimethylsilyl)silylchloride in room temperature. Homo-polymerization or co-polymerization was done using a free radical polymerization method using α,α -azobis(isobutyronitrile) (AIBN) as a initiator. Incorporation of this bulky group to polymers showed a high glass transition temperature compared to polystyrene without this group. Monomer and polymers and compositions of poly(para-sisylmethylstyrene) in co-polymers was characterized by spectroscopy. Since, some important polymer properties have been modified by incoporating silyl groups, this work can be an important case in polymer chemistry.

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Photochemical conversion and storage of solar energy by azobenzene.

Cited by 60 publications

References 0 publications

Photoswitchable Molecular Rings for Solar-Thermal Energy Storage

Photoswitchable Molecular Rings for Solar-Thermal Energy Storage

Modification of styrene polymer by attaching suitable groups as side chain

Synthesis and characterization of new monomer and polymers of hindered silyl styrene

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