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      Synthesis, Bioactivity, Molecular Docking and POM Analyses of Novel Substituted Thieno[2,3- b]thiophenes and Related Congeners

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          Abstract

          Several series of novel substituted thienothiophene derivatives were synthesized by reacting the synthone 1 with different reagents. The newly synthesized compounds were characterized by means of different spectroscopic methods such as IR, NMR, mass spectrometry and by elemental analyses. The new compounds displayed significant activity against both Gram-positive and Gram negative bacteria, in addition to fungi. Molecular docking and POM analyses show the crucial role and impact of substituents on bioactivity and indicate the unfavorable structural parameters in actual drug design: more substitution doesn’t guaranty more efficiency in bioactivity.

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          Stable polythiophene semiconductors incorporating thieno[2,3-b]thiophene.

          Maxim Shkunov, David Sparrowe, Kristijonas Genevicius … (2005)
          This work describes a new design methodology that allows the preparation of air stable, semiconducting thiophene polymers with high charge carrier mobilities. The incorporation of thieno[2,3-b]thiophene into a polythiophene backbone introduces cross-conjugated double bonds that disfavor full delocalization, leading to high ionization potential in comparison to a fully conjugated polythiophene, with no reduction in charge carrier mobility. The resulting solution processable polymers exhibit charge carrier mobilities up to 0.15 cm2/V s and on/off ratios greater than 105 when measured in air. Transistors exhibit lifetimes of several months in air with no encapsulation necessary.
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              Alkylsubstituted thienothiophene semiconducting materials: structure-property relationships.

              H. FONG, Thomas L.-M. Sørensen, Detlef-M Smilgies … (2009)
              A family of conjugated polymers with fused structures consisting of three to five thiophene rings and with the same alkyl side chains has been synthesized as a means to understand structure-property relationships. All three polymers showed well-extended conjugation through the polymer backbone. Ionization potentials (IP) ranged from 5.15 to 5.21 eV; these large values are indicative of their excellent oxidative stability. X-ray diffraction and AFM studies suggest that the polymer with the even number of fused thiophene rings forms a tight crystalline structure due to its tilted side chain arrangement. On the other hand, the polymers with the odd number of fused thiophene rings packed more loosely. Characterization in a field-effect transistor configuration showed that the mobility of the polymer with the even number of rings is 1 order of magnitude higher than its odd-numbered counterparts. Through this structure-property study, we demonstrate that proper design of the molecules and properly arranged side chain positions on the polymer backbone can greatly enhance polymer electronic properties.
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                Author and article information

                Contributors
                Derek J. McPhee: Role: Academic Editor
                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 23 January 2015
                Publication date Collection: February 2015
                Volume: 20
                Issue: 2
                Pages: 1824-1841
                Affiliations
                [1 ]Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia; E-Mail: showiman@ 123456ksu.edu.sa
                [2 ]King Abdulaziz City for Science and Technology, P.O. Box 6086, Riyadh 11442, Saudi Arabia; E-Mail: fzsw2010@ 123456hotmail.com
                [3 ]Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia 21321 Alexandria, Egypt
                [4 ]Lab of Chemical Material, Faculty of Sciences University Mohammed Premier, Oujda 60000, Morocco; E-Mail: taibi.ben.hadda@ 123456gmail.com
                [5 ]Department of Chemistry, The University of Jordan, Amman 11942, Jordan; E-Mail: mmubarak700@ 123456gmail.com
                [6 ]Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75210, Pakistan; E-Mails: mjazse@ 123456gmail.com (S.N.); zaheer.qasmi@ 123456iccs.edu (Z.U.-H.)
                [7 ]Institute of Chemical Sciences, University of Peshawar, Peshawar 25120, Pakistan; E-Mail: mashaljcs@ 123456yahoo.com
                Author notes
                [†]

                These authors contributed equally to this work.

                [* ]Authors to whom correspondence should be addressed; E-Mails: Yahia@ 123456ksu.edu.sa (Y.N.M.); ambarakat@ 123456ksu.edu.sa (A.B.); Tel.: +966-1467-5898 (Y.N.M.); +966-1467-5884 (A.B.); Fax: +966-1467-5992 (Y.N.M./A.B.).
                Article
                Publisher ID: molecules-20-01824
                DOI: 10.3390/molecules20021824
                PMC ID: 6272574
                PubMed ID: 25621424
                SO-VID: 7d33e17a-751a-48a5-82bf-b2f44792fbe6
                Copyright © © 2015 by the authors.
                License:

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/4.0/).

                History
                Date received : 17 December 2014
                Date accepted : 14 January 2015
                Categories
                Subject: Article

                Keywords: thienothiophene,antibacterial activity,antifungal activity, molecular docking,petra/osiris/molinspiration (pom) analyses
                Data availability:
                Keywords: thienothiophene, antibacterial activity, antifungal activity, molecular docking, petra/osiris/molinspiration (pom) analyses

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