Aromatization of dihydrothiophenes. Thiophenesaccharin: a sweet surprise

Rossy, P.; Hoffmann, Werner; Mueller, N.

doi:10.1021/jo01292a012

Cited by 66 publications

(11 citation statements)

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“…The conventional methods for their preparation require the formation of the diesters of 3-thioadipic acid and 4-thiopimelic acid followed by a Dieckmann condensation (1,(4)(5)(6)(7)(8). Apart from the operational complexity, these procedures often suffer from unsatisfactory yields of the products due to the rather severe conditions required to induce Dieckmann reaction.…”

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confidence: 99%

An improved procedure for the preparation of 3-carbometfaoxy-4-oxotetrahydrothiopyran, 2- and 4-carbomethoxy-3-oxotetrahydrothiophene

Liu¹,

Ngooi²

1982

Can. J. Chem.

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An improved procedure for the preparation of the title compounds 1-3 has been developed. Direct condensation of methyl 3-mercaptopropionate with methyl acrylate using sodium hydride as a base gave compound 1 in good yield. The reaction of methyl thioglycolate and methyl acrylate at 0 °C gave compound 2 as the major product whereas at lower temperature (−40 °C) isomer 3 was found as the major product. The condensation reactions of methyl thioglycolate with methyl methacrylate and crotonate were also carried out.

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confidence: 99%

An improved procedure for the preparation of 3-carbometfaoxy-4-oxotetrahydrothiopyran, 2- and 4-carbomethoxy-3-oxotetrahydrothiophene

Liu¹,

Ngooi²

1982

Can. J. Chem.

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“…The TID unit was prepared according to a modified literature procedure . In order to anchor alkyl side chains on the original artificial sweetener unit, the phase transfer catalyst 15‐crown‐5 was used to achieve a relatively high conversion yield.…”

Section: Resultsmentioning

confidence: 99%

Tuning the Polarizability in Donor Polymers with a Thiophenesaccharin Unit for Organic Photovoltaic Applications

Zheng

et al. 2014

Adv Funct Materials

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1 www.MaterialsViews.com wileyonlinelibrary.com of the relationship between polymeric structure of the donor material and device performance. Among the factors that may infl uence solar energy conversion, the nature of electron donating and accepting materials and the morphology of the composites play the crucial roles in determining the fi nal performance of the devices. In recent years, fullerene derivatives such as [6,6]-phenyl C 71 -butyric acid methyl ester (PC 71 BM) have been widely adopted as electron acceptors due to their low lying energy levels and relatively high electron affi nity and mobility. It was also found that addition of a small amount of high boiling point solvent, generally 1,8-diiodooctane (DIO), can reliably improve the morphology of most of the composite systems. [ 19,20 ] Thus, we focus our main effort on understanding the structure/property correlation of electron donor materials in order to develop innovative strategies for achieving high performance solar cells.Numerous factors can infl uence the optical and electrical properties of low bandgap polymers. Our previous research indicated that the calculated internal dipole moment change between the ground and excited states of a polymer's repeating units, Δµ ge , showed a linear correlation with solar cell performance when other factors, such as morphology and charge carrier mobility, are comparable. [ 21,22 ] Crucial questions to be answered are that what will happen when Δµ ge is further increased, and why such a phenomenological model works well in a certain range. In this paper, calculations of dipolar change based on the polymer repeating units led us to identify two polymer systems, both copolymers containing benzodithiophene (BDT). One is based on thieno[3,4-c]pyrrole-4,6-dione (TPD) and the other on 3-oxothieno[3,4-d ]isothiazole 1,1-dioxide (TID). The TPD unit has recently been incorporated into various low band gap conjugated polymer systems. [23][24][25] Previously explored as an artifi cial sweetener, TID unit bears both a sulfonyl and a carbonyl group, and is more electron defi cient than TPD. The calculation results showed that the repeating units of both polymers containing TPD and TID (PPB and PID, respectively) exhibit a larger Δµ ge than our previous champion polymer PTB7. Thus, two polymers, PPB and PID, were synthesized and characterized Tao Tuning the Polarizability in Donor Polymers with a Thiophenesaccharin Unit for Organic Photovoltaic Applications

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“…Introduction of the protected sulfur substituent was carried out by an addition/elimination process with benzylthiol. The obtained dihydro compound 6a could be aromatized according to a general procedure by treatment with SO 2 Cl 2 [7]. Electrophilic chlorination followed by elimination led to 7a.…”

Section: Resultsmentioning

confidence: 99%

A Synthetic Approach to Methyl Thieno[2,3-d][1,2,3]thiadiazole Carboxylates via Diazotation

Stanetty

Mihovilovič

1999

Monatshefte fuer Chemie

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Aromatization of dihydrothiophenes. Thiophenesaccharin: a sweet surprise

Cited by 66 publications

References 0 publications

An improved procedure for the preparation of 3-carbometfaoxy-4-oxotetrahydrothiopyran, 2- and 4-carbomethoxy-3-oxotetrahydrothiophene

An improved procedure for the preparation of 3-carbometfaoxy-4-oxotetrahydrothiopyran, 2- and 4-carbomethoxy-3-oxotetrahydrothiophene

Tuning the Polarizability in Donor Polymers with a Thiophenesaccharin Unit for Organic Photovoltaic Applications

A Synthetic Approach to Methyl Thieno[2,3-d][1,2,3]thiadiazole Carboxylates via Diazotation

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