Generation and synthetic utility of dianions derived from thiophencarboxylic acids

Knight, David W.; Nott, Andrew P.

doi:10.1039/p19830000791

Cited by 26 publications

(15 citation statements)

References 6 publications

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“…64 Lithium 5-lithiothiophene-2-carboxylate (12, Scheme 1) was prepared as previously described. 65 Thiophene-2-diethyl phosphate (13) was prepared as previously described. 66,67 Preparation of Bis(julolidyl)selenorhodamine 4-Se (Chart 1).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Selenorhodamine Dye-Sensitized Solar Cells: Influence of Structure and Surface-Anchoring Mode on Aggregation, Persistence, and Photoelectrochemical Performance

et al. 2016

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A library of six selenorhodamine dyes (4-Se-9-Se) were synthesized, characterized, and evaluated as photosensitizers of TiO2 in dye-sensitized solar cells (DSSCs). The dyes were constructed around either a bis(julolidyl)- or bis(half-julolidyl)-modified selenoxanthylium core functionalized at the 9-position with a thienyl group bearing a carboxylic, hydroxamic, or phosphonic acid for attachment to TiO2. Absorption bands of solvated dyes 4-Se-9-Se were red-shifted relative to the dimethylamino analogues. The dyes adsorbed to TiO2 as mixtures of monomeric and H-aggregated dyes, which exhibited broadened absorption spectra and increased light-harvesting efficiencies relative to the solvated monomeric dyes. Carboxylic acid-bearing dyes 4-Se and 7-Se initially exhibited the highest incident photon-to-current efficiencies (IPCEs) of 65-80% under monochromatic illumination, but the dyes desorbed rapidly from TiO2 into solutions of HCl (0.1 M) in a CH3CN:H2O mixed solvent (120:1 v:v). The hydroxamic acid- and phosphonic acid-bearing dyes 5-Se, 6-Se, 8-Se, and 9-Se exhibited lower IPCEs (49-65%) immediately after preparation of DSSCs; however, the dyes were vastly more inert on TiO2, and IPCEs decreased only minimally with successive measurements under constant illumination. Power-conversion efficiencies (PCEs) of the selenorhodamine-derived DSSCs were less than 1%, probably due to inefficient regeneration of the dyes following electron injection. For a given anchoring group, the bis(half-julolidyl) dyes exhibited higher open-circuit photovoltages and PCEs than the corresponding bis(julolidyl) dyes. The hydroxamic acid- and phosphonic acid-bearing dyes are intriguing photosensitizers of TiO2 in light of their aggregation-induced spectral broadening, high monochromatic IPCEs, and relative inertness to desorption into acidic media.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Selenorhodamine Dye-Sensitized Solar Cells: Influence of Structure and Surface-Anchoring Mode on Aggregation, Persistence, and Photoelectrochemical Performance

et al. 2016

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“…Methyl 2-amino-5-isopropyl-1,3-thiazole-4-carboxylate 14,15 (14) This compound was prepared according to a standard literature procedure 14 1-Methyl-4-nitro-1H-pyrrole-2-carboxylic acid (520 mg, 3.06 mmol) was dissolved in thionyl chloride (10 cm 3 ). The reaction mixture was heated under reflux overnight.…”

Section: Molecular Modellingmentioning

confidence: 99%

Synthesis and antimicrobial activity of some netropsin analogues

et al. 2004

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Nine novel lexitropsins were synthesized by linking two netropsin-like moieties through three different dicarboxylic acids; 9,10-dihydro-2,7-phenanthrenedicarboxylic acid; [(3-[[(carboxymethyl)amino]carbonyl]benzoyl)amino]acetic acid and indole-2,5-dicarboxylic acid. The netropsin residues were modified by the use of N-isopentylpyrrole, 5-methylthiophene or 5-isopropylthiazole heterocyclic building blocks in place of the usual N-methylpyrrole. The compounds were tested against five gram-positive bacteria: Staphylococcus aureus, Streptomyces faecalis, methicillin resistant Staphylococcus aureus, Enterobacter cloacae, Mycobacterium fortuitum, three gram-negative bacteria: Klebsiella aerogenes, Proteus vulgaris, Escherichia coli and three fungi: Aspergillus niger, Candida albicans and Aspergillus nidulans. Some of the compounds showed significant inhibitory effects on the growth of the microorganisms.

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“…Active thieno[3,2-g]quinoline-4,9-dione (8) 17 was obtained in 10% and 25% yields, respectively, when the acid 6 and its ethyl ester 7 were exposed to LTMP. The aforementioned less acidic 6 hydrogen at C3Ј and, more importantly, the facile deprotonation 18 of the thiophene ring under the conditions used could alter the course of the reaction (Scheme 6). anhydride, respectively, provided the ester 9 and the acid 10 in medium to good yields (Scheme 7).…”

Section: -(2-pyridylcarbonyl)thiophene-3-carboxylic Acid and Ethyl 2-...mentioning

confidence: 99%

Metallation of pyridines and quinolines in the presence of a remote carboxylate group. New syntheses of heterocyclic quinones

et al. 2004

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2-(3- and 2-Pyridylcarbonyl)benzoic acids (2,3), 2-(2-pyridylcarbonyl)thiophene-3-carboxylic acid (6), 2-(3-quinolylcarbonyl)benzoic acid (10), and most of the corresponding esters (compounds 1,7 and 9 ) are readily synthesized and involved in a deprotonation-condensation sequence. Biologically active aza-anthraquinones such as benzo[g]isoquinoline-5,10-dione (2-azaanthraquinone, 4 ) and benzo[g]quinoline-5,10-dione (1-azaanthraquinone, 5) are prepared using the strategy. Extension to other heterocyclic quinones such as thieno[3,2-g]quinoline-4,9-dione (8) and benzo[j]phenanthridine-7,12-dione (11) is also investigated.

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Generation and synthetic utility of dianions derived from thiophencarboxylic acids

Cited by 26 publications

References 6 publications

Selenorhodamine Dye-Sensitized Solar Cells: Influence of Structure and Surface-Anchoring Mode on Aggregation, Persistence, and Photoelectrochemical Performance

Selenorhodamine Dye-Sensitized Solar Cells: Influence of Structure and Surface-Anchoring Mode on Aggregation, Persistence, and Photoelectrochemical Performance

Synthesis and antimicrobial activity of some netropsin analogues

Metallation of pyridines and quinolines in the presence of a remote carboxylate group. New syntheses of heterocyclic quinones

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