- Luminescent lanthanide coordination polymers synthesized via in-situ hydrolysis of dimethyl-3,4-furandicarboxylate
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Dimethyl-3,4-furandicarboxylate undergoes hydrolysis under hydrothermal conditions with lanthanide (Ln) ions to form two-dimensional coordination polymers, [Ln(C6H2O5)(C6H3O5)(H2O)]n (Ln=Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu). The resulting materials exhibit luminescent properties with quantum yields and lifetimes for the Eu(III) and Tb(III) compounds of 1.1?±0.3% and 0.387?±0.0001 ms, and 3.3?±0.8% and 0.769?±0.006 ms, respectively. Energy values for the singlet and triplet states were determined for dimethyl-3,4-furandicarboxylate and 3,4-furandicarboxylic acid. Excited state dynamics and structural features are examined to explicate the reported quantum yields. A series of other FDC structures is briefly presented.
- Greig, Natalie E.,Einkauf, Jeffrey D.,Clark, Jessica M.,Corcoran, Eric J.,Karram, Joseph P.,Kent, Charles A.,Eugene, Vadine E.,Chan, Benny C.,De Lill, Daniel T.
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- THIENO, FURO AND SELENOPHENO-[3,4-C]PYRROLE-4,6-DIONE COPOLYMERS
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Novel photoactive copolymers based on thieno, furo or selenopheno-[3,4- c]pyrrole-4,6-dione-derivative are described herein. More specifically, the photoactive copolymers comprise repeating units of Formula I -[A1-A2]- I wherein A1 is an electron donating unit such as a mono or polycyclic heteroaryl that is unsubstitued or substituted with one or more C1-20-alkyl or C1-20-alkoxy; and A2 is an alkylfuro or alkylselenopheno-[3,4-c]pyrrole-4,6-dione-derivative. The photoactive copolymers are suitable for use in BHJ solar cells.
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Paragraph 00112
(2014/03/25)
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- Pd-catalyzed direct C-H arylation of thieno[3,4-c]pyrrole-4,6-dione (TPD): A step-economical synthetic alternative to access TPD-centred symmetrical small molecules
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We demonstrate a step-economical and viable synthetic alternative to access a series of thieno[3,4-c]pyrrole-4,6-dione (TPD)-based π-conjugated molecules through Pd-catalyzed direct C-H arylations. A comprehensive synthetic study including the screening of various kinds of palladium catalysts, ligands, and bases is reported. Under the optimum reaction conditions, TPD and its common derivatives underwent efficient and mild direct C-H arylations with a variety of functionalized bromoarenes. Functional groups such as ester, nitrile, ketone, aldehyde, and halide were well-tolerated, which substantially extended the reaction scope. We hope the reported method will provide materials scientists a relatively greener synthetic route to efficiently prepare TPD-containing π-functional materials. This journal is the Partner Organisations 2014.
- Chang, Shan-Yun,Lin, Po-Han,Liu, Ching-Yuan
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p. 35868 - 35878
(2014/11/07)
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- Thieno-, furo-, and selenopheno[3,4-c ]pyrrole-4,6-dione copolymers: Effect of the heteroatom on the electrooptical properties
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New push-pull conjugated polymers based on furo[3,4-c]pyrrole-4,6-dione (FPD) and selenopheno[3,4-c]pyrrole-4,6-dione (SePD) have been synthesized and compared with their thieno[3,4-c]pyrrole-4,6-dione (TPD) analogues to investigate the effects of the heteroatom on the electrooptical properties. The copolymers were synthesized using either Stille cross-coupling or direct heteroarylation polymerization (DHAP), the latter method giving high molecular weights. Hypsochromic shifts of the band gaps were observed for FPD-based copolymers (sulfur substituted by oxygen) while small bathochromic shift was observed for SePD (sulfur substituted by selenium) when compared to its TPD analogue. These two new classes of conjugated polymers exhibit electrooptical properties that could lead to interesting bulk heterojunction plastic solar cells.
- Beaupre, Serge,Pron, Agnieszka,Drouin, Simon H.,Najari, Ahmed,Mercier, Lauren G.,Robitaille, Amelie,Leclerc, Mario
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p. 6906 - 6914,9
(2020/08/24)
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- Synthesis and biological activity of Δ-5,6-norcantharimides: importance of the 5,6-bridge
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Cantharidin (1) and norcantharidin (2) are potent protein phosphatase 1 and 2A inhibitors that also display high levels of anticancer activity against a broad range of tumor cells lines. Surprisingly, Δ-5,6-ethyl norcantharidin (3, cis-tetrahydrofurano[3,4-c]furan-1,3-dione) displays neither phosphatase inhibition nor anticancer activity. This suggests that the 5,6-ethyl bridge is pivotal to both anti-cancer and protein phosphatase activity. Additionally bioisosteric replacement of the ethereal oxygen has no effect on biological activity nor does modification of the anhydride moiety. Unlike the parent norcantharidin, anhydride ring opening has no effect on either protein phosphatase inhibition or anti-cancer activity. Additionally, this work highlights the discovery of the octyl substituted, cis-5-benzyl-2-hexyltetrahydro-2H,3aH-pyrrolo[3,4-c]pyrrole-1,3-dione, 9p, and the octyl substituted, cis-octyltetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione, 8p, as two new cytotoxic agents which are equipotent (9p) with, and more potent (8p) than norcantharidin. Crown Copyright
- Thaqi, Ali,Scott, Janet L.,Gilbert, Jayne,Sakoff, Jennette A.,McCluskey, Adam
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supporting information; experimental part
p. 1717 - 1723
(2010/07/02)
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- The facile generation of a tetramethyleneethane type radical cation and biradical utilizing a 3,4-di(α-styryl)furan and a photoinduced ET and back ET sequence
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Product analyses and nanosecond time-resolved spectroscopy on laser flash photolysis were studied for the photoinduced electron-transfer reaction of 3,4-di(α-styryl)furan (6a). A combination of these results, kinetic, density functional theoretical (DFT), and time-dependent DFT analyses enabled assignment of the absorption to the tetramethyleneethane (TME)-type radical cation (7a?+, λmax = 392 nm) and the corresponding singlet biradical (17a??, λmax = 661 nm). These two intermediates were mechanistically linked to each other with a facile back electron-transfer reaction. The present studies provide a new method for the generation of aryl-substituted TME-type intermediates.
- Ikeda, Teruyo,Ikeda, Hiroshi,Takahashi, Yasutake,Yamada, Masafumi,Mizuno, Kazuhiko,Tero-Kubota, Shozo,Yamauchi, Seigo
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p. 2466 - 2472
(2008/09/18)
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- The synthesis of 6,9-bis[(aminoalkyl)amino] substituted benzo[g]quinoxaline-, benzo[g]quinazoline- and benzo[g]phthalazine-5,10- diones via regiospecific displacements
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The synthesis of 6,9-difluoro substituted benzo[g]quinoxaline-5,10-diones (3A), benzo[g]quinazoline-5,10-diones (3B) and benzo[g]phthalazine-5,10- diones (3C) have been accomplished. Treatment of 3A, 3B or 3C with diamines or N-(t-butoxycarbonyl)ethylenediamine led to the corresponding 6,9- bis[(aminoalkyl)amino]-substituted analogues related to 2A, 2B and 2C, respectively. The mono-substituted derivatives 4h and 4i could be isolated from displacements commencing from 3A. A competitive ring-opening of the pyrimidine ring of 2C occurred during the reaction with N,N- dimethylethylenediamine. Removal of the BOC-protecting group from 2Ac led to the hydrochloride salt 2Ab. A novel synthetic pathway to 6,9- dihydroxybenzo[g]phthalazine-5,10-dione (21a) was developed. Conversion of 21a to the ditosylate 21b was readily accomplished. Treatment of 21b with N,N-dimethylethylenediamine or N-(t-butoxycarbonyl)ethylenediamine led to 2Ca and 2Cc, respectively. Removal of the BOC-protecting group from 2Cc with trifluoroacetic acid followed by ion-exchange led to the hydrochloride salt 2Cb. Treatment of ditosylate 21b with N-(t-butoxycarbonyl)ethylenediamine also led to the mono-substituted analogue 25a along with a small amount of the O-S cleavage product 25b. Treatment of 25a with N,N- dimethylethylenediamine led to the unsymmetrically substituted derivative 25c which was converted into the trifluoroacetate salt 25d.
- Krapcho,Maresch,Helgason,Rosner,Hacker,Spinelli,Menta,Oliva
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p. 1597 - 1606
(2007/10/02)
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- SYNTHESIS OF NECTRIAFURONE, AN ISOFURANONAPHTHOQUINONE ISOLATED FROM THE FUNGUS NECTRIA HAEMATOCOCCA
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Syntheses of 5-methoxy-4,7-dihydroxynaphtho8,9-furandione (2) and of 4,7-dihydroxynaphtho8,9-furadione (3) were carried out by rapid Friedel-Crafts reaction using the dry method.The addition of acetaldehyde on 2 in presence of LDA gave the (+/-)-nectriafurone (1), thus confirming the proposed structure of 3-(1'-hydroxyethyl)-5-methoxy-4,7-dihydroxynaphtho8,9-furandione.
- Devys, Michel,Barbier, Michel,Parisot, Denise
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p. 1485 - 1490
(2007/10/02)
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- 1,1-Alkanediol dicarboxylate linked antibacterial agents
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Useful antibacterial agents in which a penicillin and/or a beta-lactamase inhibitor are linked via 1,1-alkanediol dicarboxylates are of the formula STR1 where A is the residue of certain dicarboxyic acids, R3 is H or (C1 -C3), n is zero or 1 such that when n is zero R is P or B and R1 is the residue of certain esters, H or a salt thereof; and when n is 1, one of R and R1 is P and the other is B, and P is STR2 where R2 is H or certain acyl groups, and B is the residue of a beta-lactamase inhibiting carboxylic acid; a method for their use, pharmaceutical compositions thereof and intermediates useful in their production.
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