Examination of reactivity of protonated and deprotonated 2,5-dimercapto-1,3,4-thiadiazole and its derivatives by electrochemical experiment and semiempirical MO calculation

Shouji, Eiichi; Matsui, Hiroshi; Oyama, Noboru

doi:10.1016/s0022-0728(96)04757-2

Cited by 39 publications

(59 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[9] The result provided a new strategy to develop an iodine-free redox couple and also showed application in flexible DSCs. 2-mercapto-5-methyl-1,3,4-thiadiazole (McMT) derivatives have been intensely studied owing to their interesting electrochemical behavior [10] and also potential application for photovoltaic devices. [11] Herein, we adopt an organic redox couple consisting of the thiolate form To determine the standard redox potential of McMT À / BMT, cyclic voltammetry (CV) was performed using 0.2 m lithium perchlorate (LiClO 4 ) as supporting electrolyte.…”

mentioning

confidence: 99%

Efficient Organic‐Dye‐Sensitized Solar Cells Based on an Iodine‐Free Electrolyte

Tian¹,

Jiang²,

Yu³

et al. 2010

Angewandte Chemie

View full text Add to dashboard Cite

Dye-sensitized solar cells (DSCs) have been investigated intensely since Grätzel and ORegan reported significant improvements in 1991, [1] thus manifesting DSCs as a new promising type of solar energy-to-electricity conversion device. To further improve the energy conversion efficiency and stability, many efforts have been made to optimize different components of DSCs. Although the traditional electrolyte based on the iodide/triiodide (I À /I 3 À ) redox couple works efficiently in DSCs, the disadvantages, such as corrosion of metal-based current collectors (for example silver, copper), sublimation of iodine, and absorption of visible light, limit the large scale production and commercial application of DSCs. Therefore, as a central component of such devices, the electrolyte has been widely studied. Finding an alternative redox couple plays a crucial role in the future development of DSCs. To date, metal complexes, [2] hole conductors, [3] p-type semiconductors,À , [7] and also organic radicals (TEMPO) [8] have been introduced to DSCs as redox mediators for dye regeneration. However, DSCs based on these redox couples typically show lower efficiencies than those employing the I À / I 3 À electrolyte, and most of them also present safety issues.The reasons why these new redox couples seemingly cannot match the performance of the I À /I 3 À couple can probably be attributed to higher recombination losses, higher chargetransfer resistance at the counter-electrode, and/or masstransport limitations. Recently, Grätzel and co-workers reported an organic redox couple derived from 5-mercapto-1-methyltetrazole, which gave an efficiency of 6.4 % with Z907Na-based DSCs under standard illumination conditions (100 mW cm À2 ).[9] The result provided a new strategy to develop an iodine-free redox couple and also showed application in flexible DSCs. 2-mercapto-5-methyl-1,3,4-thiadiazole (McMT) derivatives have been intensely studied owing to their interesting electrochemical behavior [10] and also potential application for photovoltaic devices.[11] Herein, we adopt an organic redox couple consisting of the thiolate form (McMT

show abstract

mentioning

confidence: 99%

Efficient Organic‐Dye‐Sensitized Solar Cells Based on an Iodine‐Free Electrolyte

Tian¹,

Jiang²,

Yu³

et al. 2010

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

“…On the other hand, the oxidation potential of DBDS is higher than that of DEDT, suggesting that the active species may not be produced during the polymerization of DEDT by electrochemical oxidation. [15,16] However, the electrochemical reduction of disulfide bonds of DBDS is likely to occur. During the course of the reduction, the active species, which is presumably the thiyl radical, should participate in the polymerization.…”

Section: Additive Effect Of Dbds and Bzsh On The Polymerization Of Dedtmentioning

confidence: 99%

Electrochemical Polymerization of 1,10-Decanedithiol in CH3CN at Constant Current

Endo

2002

Macromol. Chem. Phys.

View full text Add to dashboard Cite

“…6 There have also been studies of the redox behavior of DMcT and its derivatives in various solvent systems and of the spectroscopic changes that accompany the redox transformations of DMcT and its disulfide dimmer. [7][8][9][10] Figure 1 shows the redox couple for DMcT, illustrating that it exists in a monomeric form in the reduced state and forms a polymer containing disulfide linkages after oxidation. The question of the protonation state of the reduced, monomeric material of DMcT in these films (i.e.…”

Section: Introductionmentioning

confidence: 99%

Direct evidence of redox mediation between a poly(aniline-co-N-propanesulfonic acid aniline) and 2,5-dimercapto-1,3,4-thiadiazole by UV-visible reflectance spectroscopy

Buttry¹,

Torresi²,

Torresi³

2002

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

Neste trabalho é apresentado um estudo espectroeletroquímico do comportamento redox de filmes finos de um derivado de polianilina sulfonada, poli(anilina-coN -ácido propanosulfônico anilina), (PAPSAH) e uma mistura do mesmo derivado com 2,5-dimercapto-1,3,4-tiodiazol (DMcT) por reflectância e transmissão no UV-visível. O estudo mostra as mudanças diferenciais espectrais que acompanham a oxidação da PAPSAH e consistem no incremento da banda polarônica a 400 nm e o crescimento de uma banda a 600 nm. No processo de redução da PAPSAH, a diminuição das mesmas duas bandas é observado, mostrando que estas mudanças com o potencial são reversíveis. No caso do filme misto PAPSAH/DMcT, os dados também revelam mudanças espectrais características da oxidação do DMcT para produzir um polímero de disulfeto durante a oxidação da PAPSAH. Estas mudanças são também reversíveis com o potencial. Estes dados são a primeira evidencia espectroscópica direta da mediação redox entre um derivado de poli(anilina) e o DMcT. A UV-visible reflectance and transmission spectroelectrochemical study of the redox behavior of thin films of a sulfonated polyaniline derivative, poly(aniline-coN -propanesulfonic acid aniline) (PAPSAH) and of a mixture of this same derivative and 2,5-dimercapto-1,3,4-thiadiazole (DMcT) is reported. The study shows the differential spectral changes that accompany the oxidation of PAPSAH, which comprise increases in the polaron band at 400 nm and a band at 600 nm. The reduction process of PAPSAH, comprises decreases in these same spectral bands. These changes are shown to be reversible with potential. For the case of the PAPSAH/DMcT mixed film, the data also reveal spectral changes that are characteristic of oxidation of DMcT to produce a disulfide polymer during PAPSAH oxidation. These changes are also reversible with potential. These data represent the first direct, spectroscopic observation of the redox mediation between a polyaniline derivative and DMcT.

show abstract

Examination of reactivity of protonated and deprotonated 2,5-dimercapto-1,3,4-thiadiazole and its derivatives by electrochemical experiment and semiempirical MO calculation

Cited by 39 publications

References 11 publications

Efficient Organic‐Dye‐Sensitized Solar Cells Based on an Iodine‐Free Electrolyte

Efficient Organic‐Dye‐Sensitized Solar Cells Based on an Iodine‐Free Electrolyte

Electrochemical Polymerization of 1,10-Decanedithiol in CH3CN at Constant Current

Direct evidence of redox mediation between a poly(aniline-co-N-propanesulfonic acid aniline) and 2,5-dimercapto-1,3,4-thiadiazole by UV-visible reflectance spectroscopy

Contact Info

Product

Resources

About