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Single and Twofold Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Thiophenes.

Angewandte Chemie (International ed. in English)

Wiebe A, Lips S, Schollmeyer D, Franke R, Waldvogel SR.
PMID: 28967700
Angew Chem Int Ed Engl. 2017 Nov 13;56(46):14727-14731. doi: 10.1002/anie.201708946. Epub 2017 Oct 20.

The first electrochemical dehydrogenative C-C cross-coupling of thiophenes with phenols has been realized. This sustainable and very simple to perform anodic coupling reaction enables access to two classes of compounds of significant interest. The scope for electrochemical C-H-activating cross-coupling...

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Wiebe A, Lips S, Schollmeyer D, et al. Single and Twofold Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Thiophenes. Angew Chem Int Ed Engl. 2017;56(46):14727-14731doi: 10.1002/anie.201708946.
Wiebe, A., Lips, S., Schollmeyer, D., Franke, R., & Waldvogel, S. R. (2017). Single and Twofold Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Thiophenes. Angewandte Chemie (International ed. in English), 56(46), 14727-14731. https://doi.org/10.1002/anie.201708946
Wiebe, Anton, et al. "Single and Twofold Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Thiophenes." Angewandte Chemie (International ed. in English) vol. 56,46 (2017): 14727-14731. doi: https://doi.org/10.1002/anie.201708946
Wiebe A, Lips S, Schollmeyer D, Franke R, Waldvogel SR. Single and Twofold Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Thiophenes. Angew Chem Int Ed Engl. 2017 Nov 13;56(46):14727-14731. doi: 10.1002/anie.201708946. Epub 2017 Oct 20. PMID: 28967700.
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Dual role of Rh(III) catalyst enables regioselective halogenation of (electron-rich) heterocycles.

Journal of the American Chemical Society

Schröder N, Lied F, Glorius F.
PMID: 25590585
J Am Chem Soc. 2015 Feb 04;137(4):1448-51. doi: 10.1021/jacs.5b00283. Epub 2015 Jan 27.

The Rh(III)-catalyzed selective bromination and iodination of electron-rich heterocycles is reported. Kinetic investigations show that Rh plays a dual role in the bromination, catalyzing the directed halogenation and preventing the inherent halogenation of these substrates. As a result, this...

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Schröder N, Lied F, Glorius F. Dual role of Rh(III) catalyst enables regioselective halogenation of (electron-rich) heterocycles. J Am Chem Soc. 2015;137(4):1448-51doi: 10.1021/jacs.5b00283.
Schröder, N., Lied, F., & Glorius, F. (2015). Dual role of Rh(III) catalyst enables regioselective halogenation of (electron-rich) heterocycles. Journal of the American Chemical Society, 137(4), 1448-51. https://doi.org/10.1021/jacs.5b00283
Schröder, Nils, et al. "Dual role of Rh(III) catalyst enables regioselective halogenation of (electron-rich) heterocycles." Journal of the American Chemical Society vol. 137,4 (2015): 1448-51. doi: https://doi.org/10.1021/jacs.5b00283
Schröder N, Lied F, Glorius F. Dual role of Rh(III) catalyst enables regioselective halogenation of (electron-rich) heterocycles. J Am Chem Soc. 2015 Feb 04;137(4):1448-51. doi: 10.1021/jacs.5b00283. Epub 2015 Jan 27. PMID: 25590585.
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Regioselective oxidative Pd-catalysed coupling of alkylboronic acids with pyridin-2-yl-substituted heterocycles.

Chemical communications (Cambridge, England)

Wippich J, Schnapperelle I, Bach T.
PMID: 25605647
Chem Commun (Camb). 2015 Feb 21;51(15):3166-8. doi: 10.1039/c4cc10144h.

A total of 19 alkylated heterocycles (thiophenes, benzothiophenes, pyrroles, furans) were prepared (36-99% yield) from the respective pyridin-2-yl-substituted precursors employing alkylboronic acids as the C-H alkylating reagents in an oxidative (Ag2CO3 and 2,6-dimethyl-1,4-benzoquinone as oxidants) Pd-catalysed coupling reaction.

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Wippich J, Schnapperelle I, Bach T. Regioselective oxidative Pd-catalysed coupling of alkylboronic acids with pyridin-2-yl-substituted heterocycles. Chem Commun (Camb). 2015;51(15):3166-8doi: 10.1039/c4cc10144h.
Wippich, J., Schnapperelle, I., & Bach, T. (2015). Regioselective oxidative Pd-catalysed coupling of alkylboronic acids with pyridin-2-yl-substituted heterocycles. Chemical communications (Cambridge, England), 51(15), 3166-8. https://doi.org/10.1039/c4cc10144h
Wippich, Julian, et al. "Regioselective oxidative Pd-catalysed coupling of alkylboronic acids with pyridin-2-yl-substituted heterocycles." Chemical communications (Cambridge, England) vol. 51,15 (2015): 3166-8. doi: https://doi.org/10.1039/c4cc10144h
Wippich J, Schnapperelle I, Bach T. Regioselective oxidative Pd-catalysed coupling of alkylboronic acids with pyridin-2-yl-substituted heterocycles. Chem Commun (Camb). 2015 Feb 21;51(15):3166-8. doi: 10.1039/c4cc10144h. PMID: 25605647.
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Regioselective synthesis of 2-(bromomethyl)-5-aryl-thiophene derivatives via palladium (0) catalyzed suzuki cross-coupling reactions: as antithrombotic and haemolytically active molecules.

Chemistry Central journal

Rizwan K, Zubair M, Rasool N, Ali S, Zahoor AF, Rana UA, Khan SU, Shahid M, Zia-Ul-Haq M, Jaafar HZ.
PMID: 25685184
Chem Cent J. 2014 Dec 17;8:74. doi: 10.1186/s13065-014-0074-z. eCollection 2014.

BACKGROUND: It is seen that the regioselective functionalizations of halogenated heterocycles play an important role in the synthesis of several types of organic compounds. In this domain, the Suzuki-Miyaura reaction has emerged as a convenient way to build carbon-carbon...

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Rizwan K, Zubair M, Rasool N, et al. Regioselective synthesis of 2-(bromomethyl)-5-aryl-thiophene derivatives via palladium (0) catalyzed suzuki cross-coupling reactions: as antithrombotic and haemolytically active molecules. Chem Cent J. 2014;8:74doi: 10.1186/s13065-014-0074-z.
Rizwan, K., Zubair, M., Rasool, N., Ali, S., Zahoor, A. F., Rana, U. A., Khan, S. U., Shahid, M., Zia-Ul-Haq, M., & Jaafar, H. Z. (2014). Regioselective synthesis of 2-(bromomethyl)-5-aryl-thiophene derivatives via palladium (0) catalyzed suzuki cross-coupling reactions: as antithrombotic and haemolytically active molecules. Chemistry Central journal, 874. https://doi.org/10.1186/s13065-014-0074-z
Rizwan, Komal, et al. "Regioselective synthesis of 2-(bromomethyl)-5-aryl-thiophene derivatives via palladium (0) catalyzed suzuki cross-coupling reactions: as antithrombotic and haemolytically active molecules." Chemistry Central journal vol. 8 (2014): 74. doi: https://doi.org/10.1186/s13065-014-0074-z
Rizwan K, Zubair M, Rasool N, Ali S, Zahoor AF, Rana UA, Khan SU, Shahid M, Zia-Ul-Haq M, Jaafar HZ. Regioselective synthesis of 2-(bromomethyl)-5-aryl-thiophene derivatives via palladium (0) catalyzed suzuki cross-coupling reactions: as antithrombotic and haemolytically active molecules. Chem Cent J. 2014 Dec 17;8:74. doi: 10.1186/s13065-014-0074-z. eCollection 2014. PMID: 25685184; PMCID: PMC4326645.
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Visible-light-mediated C2-amination of thiophenes by using DDQ as an organophotocatalyst.

Chemical communications (Cambridge, England)

Song C, Yi H, Dou B, Li Y, Singh AK, Lei A.
PMID: 28294249
Chem Commun (Camb). 2017 Mar 28;53(26):3689-3692. doi: 10.1039/c7cc01339f.

In this work, a direct C-H activation of thiophenes was presented via an oxidation pathway under visible-light irradiation, in which the thiophene radical cation serves as the key intermediate. Various thiophenes and azoles could be transformed into the corresponding...

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Song C, Yi H, Dou B, et al. Visible-light-mediated C2-amination of thiophenes by using DDQ as an organophotocatalyst. Chem Commun (Camb). 2017;53(26):3689-3692doi: 10.1039/c7cc01339f.
Song, C., Yi, H., Dou, B., Li, Y., Singh, A. K., & Lei, A. (2017). Visible-light-mediated C2-amination of thiophenes by using DDQ as an organophotocatalyst. Chemical communications (Cambridge, England), 53(26), 3689-3692. https://doi.org/10.1039/c7cc01339f
Song, Chunlan, et al. "Visible-light-mediated C2-amination of thiophenes by using DDQ as an organophotocatalyst." Chemical communications (Cambridge, England) vol. 53,26 (2017): 3689-3692. doi: https://doi.org/10.1039/c7cc01339f
Song C, Yi H, Dou B, Li Y, Singh AK, Lei A. Visible-light-mediated C2-amination of thiophenes by using DDQ as an organophotocatalyst. Chem Commun (Camb). 2017 Mar 28;53(26):3689-3692. doi: 10.1039/c7cc01339f. PMID: 28294249.
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A One-Pot Assembly of Fully Substituted Alkyl 5-Aminothiophene-2-carboxylates from Allenes, Isothiocyanates, and Alkyl 2-Bromoacetates.

The Journal of organic chemistry

Nedolya NA, Tarasova OA, Albanov AI, Trofimov BA.
PMID: 28636379
J Org Chem. 2017 Jul 21;82(14):7519-7528. doi: 10.1021/acs.joc.7b01217. Epub 2017 Jul 05.

A novel simple approach to highly functionalized multisubstituted thiophenes such as alkyl 4-alkoxy-5-amino-3-methylthiophene-2-carboxylates through the one-pot sequential reaction of α-lithiated alkoxyallenes with isothiocyanates and alkyl 2-bromoacetates has been discovered. The process proceeds quickly (30-45 min) via in situ formation...

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Nedolya NA, Tarasova OA, Albanov AI, et al. A One-Pot Assembly of Fully Substituted Alkyl 5-Aminothiophene-2-carboxylates from Allenes, Isothiocyanates, and Alkyl 2-Bromoacetates. J Org Chem. 2017;82(14):7519-7528doi: 10.1021/acs.joc.7b01217.
Nedolya, N. A., Tarasova, O. A., Albanov, A. I., & Trofimov, B. A. (2017). A One-Pot Assembly of Fully Substituted Alkyl 5-Aminothiophene-2-carboxylates from Allenes, Isothiocyanates, and Alkyl 2-Bromoacetates. The Journal of organic chemistry, 82(14), 7519-7528. https://doi.org/10.1021/acs.joc.7b01217
Nedolya, Nina A, et al. "A One-Pot Assembly of Fully Substituted Alkyl 5-Aminothiophene-2-carboxylates from Allenes, Isothiocyanates, and Alkyl 2-Bromoacetates." The Journal of organic chemistry vol. 82,14 (2017): 7519-7528. doi: https://doi.org/10.1021/acs.joc.7b01217
Nedolya NA, Tarasova OA, Albanov AI, Trofimov BA. A One-Pot Assembly of Fully Substituted Alkyl 5-Aminothiophene-2-carboxylates from Allenes, Isothiocyanates, and Alkyl 2-Bromoacetates. J Org Chem. 2017 Jul 21;82(14):7519-7528. doi: 10.1021/acs.joc.7b01217. Epub 2017 Jul 05. PMID: 28636379.
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Terthiophene-based D-A polymer with an asymmetric arrangement of alkyl chains that enables efficient polymer solar cells.

Journal of the American Chemical Society

Hu H, Jiang K, Yang G, Liu J, Li Z, Lin H, Liu Y, Zhao J, Zhang J, Huang F, Qu Y, Ma W, Yan H.
PMID: 26515301
J Am Chem Soc. 2015 Nov 11;137(44):14149-57. doi: 10.1021/jacs.5b08556. Epub 2015 Oct 30.

We report a series of difluorobenzothiadizole (ffBT) and oligothiophene-based polymers with the oligothiophene unit being quaterthiophene (T4), terthiophene (T3), and bithiophene (T2). We demonstrate that a polymer based on ffBT and T3 with an asymmetric arrangement of alkyl chains...

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Hu H, Jiang K, Yang G, et al. Terthiophene-based D-A polymer with an asymmetric arrangement of alkyl chains that enables efficient polymer solar cells. J Am Chem Soc. 2015;137(44):14149-57doi: 10.1021/jacs.5b08556.
Hu, H., Jiang, K., Yang, G., Liu, J., Li, Z., Lin, H., Liu, Y., Zhao, J., Zhang, J., Huang, F., Qu, Y., Ma, W., & Yan, H. (2015). Terthiophene-based D-A polymer with an asymmetric arrangement of alkyl chains that enables efficient polymer solar cells. Journal of the American Chemical Society, 137(44), 14149-57. https://doi.org/10.1021/jacs.5b08556
Hu, Huawei, et al. "Terthiophene-based D-A polymer with an asymmetric arrangement of alkyl chains that enables efficient polymer solar cells." Journal of the American Chemical Society vol. 137,44 (2015): 14149-57. doi: https://doi.org/10.1021/jacs.5b08556
Hu H, Jiang K, Yang G, Liu J, Li Z, Lin H, Liu Y, Zhao J, Zhang J, Huang F, Qu Y, Ma W, Yan H. Terthiophene-based D-A polymer with an asymmetric arrangement of alkyl chains that enables efficient polymer solar cells. J Am Chem Soc. 2015 Nov 11;137(44):14149-57. doi: 10.1021/jacs.5b08556. Epub 2015 Oct 30. PMID: 26515301.
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Diversity and role of plasmids in adaptation of bacteria inhabiting the Lubin copper mine in Poland, an environment rich in heavy metals.

Frontiers in microbiology

Dziewit L, Pyzik A, Szuplewska M, Matlakowska R, Mielnicki S, Wibberg D, Schlüter A, Pühler A, Bartosik D.
PMID: 26074880
Front Microbiol. 2015 Mar 03;6:152. doi: 10.3389/fmicb.2015.00152. eCollection 2015.

The Lubin underground mine, is one of three mining divisions in the Lubin-Glogow Copper District in Lower Silesia province (Poland). It is the source of polymetallic ore that is rich in copper, silver and several heavy metals. Black shale...

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Dziewit L, Pyzik A, Szuplewska M, et al. Diversity and role of plasmids in adaptation of bacteria inhabiting the Lubin copper mine in Poland, an environment rich in heavy metals. Front Microbiol. 2015;6:152doi: 10.3389/fmicb.2015.00152.
Dziewit, L., Pyzik, A., Szuplewska, M., Matlakowska, R., Mielnicki, S., Wibberg, D., Schlüter, A., Pühler, A., & Bartosik, D. (2015). Diversity and role of plasmids in adaptation of bacteria inhabiting the Lubin copper mine in Poland, an environment rich in heavy metals. Frontiers in microbiology, 6152. https://doi.org/10.3389/fmicb.2015.00152
Dziewit, Lukasz, et al. "Diversity and role of plasmids in adaptation of bacteria inhabiting the Lubin copper mine in Poland, an environment rich in heavy metals." Frontiers in microbiology vol. 6 (2015): 152. doi: https://doi.org/10.3389/fmicb.2015.00152
Dziewit L, Pyzik A, Szuplewska M, Matlakowska R, Mielnicki S, Wibberg D, Schlüter A, Pühler A, Bartosik D. Diversity and role of plasmids in adaptation of bacteria inhabiting the Lubin copper mine in Poland, an environment rich in heavy metals. Front Microbiol. 2015 Mar 03;6:152. doi: 10.3389/fmicb.2015.00152. eCollection 2015. PMID: 26074880; PMCID: PMC4447125.
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Rhodium Thiavinyl Carbenes from 1,2,3-Thiadiazoles Enable Modular Synthesis of Multisubstituted Thiophenes.

Organic letters

Kurandina D, Gevorgyan V.
PMID: 27015356
Org Lett. 2016 Apr 15;18(8):1804-7. doi: 10.1021/acs.orglett.6b00541. Epub 2016 Mar 25.

The rhodium-catalyzed transannulation reaction between 1,2,3-thiadiazoles and alkynes, proceeding via intermediacy of the previously unknown Rh thiavinyl carbene, toward a highly efficient and regioselective synthesis of up to fully substituted thiophenes is described.

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Kurandina D, Gevorgyan V. Rhodium Thiavinyl Carbenes from 1,2,3-Thiadiazoles Enable Modular Synthesis of Multisubstituted Thiophenes. Org Lett. 2016;18(8):1804-7doi: 10.1021/acs.orglett.6b00541.
Kurandina, D., & Gevorgyan, V. (2016). Rhodium Thiavinyl Carbenes from 1,2,3-Thiadiazoles Enable Modular Synthesis of Multisubstituted Thiophenes. Organic letters, 18(8), 1804-7. https://doi.org/10.1021/acs.orglett.6b00541
Kurandina, Daria, and Gevorgyan, Vladimir. "Rhodium Thiavinyl Carbenes from 1,2,3-Thiadiazoles Enable Modular Synthesis of Multisubstituted Thiophenes." Organic letters vol. 18,8 (2016): 1804-7. doi: https://doi.org/10.1021/acs.orglett.6b00541
Kurandina D, Gevorgyan V. Rhodium Thiavinyl Carbenes from 1,2,3-Thiadiazoles Enable Modular Synthesis of Multisubstituted Thiophenes. Org Lett. 2016 Apr 15;18(8):1804-7. doi: 10.1021/acs.orglett.6b00541. Epub 2016 Mar 25. PMID: 27015356.
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Novel Carbazole (Cbz)-Based Carboxylated Functional Monomers: Design, Synthesis, and Characterization.

ChemistryOpen

Mondal E, Lellouche JP, Naddaka M.
PMID: 26478845
ChemistryOpen. 2015 Aug;4(4):489-96. doi: 10.1002/open.201500059. Epub 2015 Apr 30.

A series of novel functional carbazole (Cbz)-based carboxylated monomers were synthesized and characterized. A Clauson-Kaas procedure, a deprotection step, amide coupling, and hydrolysis were utilized as key chemical reactions towards the multistep synthesis of monomers in good to excellent...

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Mondal E, Lellouche JP, Naddaka M. Novel Carbazole (Cbz)-Based Carboxylated Functional Monomers: Design, Synthesis, and Characterization. ChemistryOpen. 2015;4(4):489-96doi: 10.1002/open.201500059.
Mondal, E., Lellouche, J. P., & Naddaka, M. (2015). Novel Carbazole (Cbz)-Based Carboxylated Functional Monomers: Design, Synthesis, and Characterization. ChemistryOpen, 4(4), 489-96. https://doi.org/10.1002/open.201500059
Mondal, Ejabul, et al. "Novel Carbazole (Cbz)-Based Carboxylated Functional Monomers: Design, Synthesis, and Characterization." ChemistryOpen vol. 4,4 (2015): 489-96. doi: https://doi.org/10.1002/open.201500059
Mondal E, Lellouche JP, Naddaka M. Novel Carbazole (Cbz)-Based Carboxylated Functional Monomers: Design, Synthesis, and Characterization. ChemistryOpen. 2015 Aug;4(4):489-96. doi: 10.1002/open.201500059. Epub 2015 Apr 30. PMID: 26478845; PMCID: PMC4603411.
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An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors.

Chemistry (Weinheim an der Bergstrasse, Germany)

Wu FP, Un HI, Li Y, Hu H, Yuan Y, Yang B, Xiao K, Chen W, Wang JY, Jiang ZQ, Pei J, Liao LS.
PMID: 28875516
Chemistry. 2017 Oct 20;23(59):14723-14727. doi: 10.1002/chem.201703415. Epub 2017 Oct 09.

A new electron-deficient unit with a fused 5-membered heterocyclic ring was developed by replacing a cyclopenta-1,3-diene from electron-rich donor indacenodithiophene (IDT) with a cyclohepta-4,6-diene-1,3-diimde unit. The imide bridge endows dithienylbenzenebisimide (BBI) with a fixed planar configuration and low energy...

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Wu FP, Un HI, Li Y, et al. An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors. Chemistry. 2017;23(59):14723-14727doi: 10.1002/chem.201703415.
Wu, F. P., Un, H. I., Li, Y., Hu, H., Yuan, Y., Yang, B., Xiao, K., Chen, W., Wang, J. Y., Jiang, Z. Q., Pei, J., & Liao, L. S. (2017). An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors. Chemistry (Weinheim an der Bergstrasse, Germany), 23(59), 14723-14727. https://doi.org/10.1002/chem.201703415
Wu, Fu-Peng, et al. "An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 23,59 (2017): 14723-14727. doi: https://doi.org/10.1002/chem.201703415
Wu FP, Un HI, Li Y, Hu H, Yuan Y, Yang B, Xiao K, Chen W, Wang JY, Jiang ZQ, Pei J, Liao LS. An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors. Chemistry. 2017 Oct 20;23(59):14723-14727. doi: 10.1002/chem.201703415. Epub 2017 Oct 09. PMID: 28875516.
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Design and Synthesis of Mixed Oligomers with Thiophenes, Dithienothiophene S,S-Dioxides, Thieno[3,4]pyrazines and 2,1,3-Benzothiadiazoles: Flipper Screening for Mechanosensitive Systems.

ChemistryOpen

Verolet Q, Soleimanpour S, Fujisawa K, Dal Molin M, Sakai N, Matile S.
PMID: 26246986
ChemistryOpen. 2015 Jun;4(3):264-7. doi: 10.1002/open.201402139. Epub 2015 Feb 05.

Monomers with large surface area and high quantum yield, that is fluorescent flippers, have been engineered into twisted push-pull oligomers to create membrane probes with high mechanosensitivity and long fluorescence lifetime. Here, the synthesis and characterization of thieno[3,4]pyrazines and...

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Verolet Q, Soleimanpour S, Fujisawa K, et al. Design and Synthesis of Mixed Oligomers with Thiophenes, Dithienothiophene S,S-Dioxides, Thieno[3,4]pyrazines and 2,1,3-Benzothiadiazoles: Flipper Screening for Mechanosensitive Systems. ChemistryOpen. 2015;4(3):264-7doi: 10.1002/open.201402139.
Verolet, Q., Soleimanpour, S., Fujisawa, K., Dal Molin, M., Sakai, N., & Matile, S. (2015). Design and Synthesis of Mixed Oligomers with Thiophenes, Dithienothiophene S,S-Dioxides, Thieno[3,4]pyrazines and 2,1,3-Benzothiadiazoles: Flipper Screening for Mechanosensitive Systems. ChemistryOpen, 4(3), 264-7. https://doi.org/10.1002/open.201402139
Verolet, Quentin, et al. "Design and Synthesis of Mixed Oligomers with Thiophenes, Dithienothiophene S,S-Dioxides, Thieno[3,4]pyrazines and 2,1,3-Benzothiadiazoles: Flipper Screening for Mechanosensitive Systems." ChemistryOpen vol. 4,3 (2015): 264-7. doi: https://doi.org/10.1002/open.201402139
Verolet Q, Soleimanpour S, Fujisawa K, Dal Molin M, Sakai N, Matile S. Design and Synthesis of Mixed Oligomers with Thiophenes, Dithienothiophene S,S-Dioxides, Thieno[3,4]pyrazines and 2,1,3-Benzothiadiazoles: Flipper Screening for Mechanosensitive Systems. ChemistryOpen. 2015 Jun;4(3):264-7. doi: 10.1002/open.201402139. Epub 2015 Feb 05. PMID: 26246986; PMCID: PMC4522174.
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