Synthesis, structures, and properties of 2,5-dianthrylthiophene derivatives

The title thiophene derivatives bearing two 9-, 1-, or 2-anthryl groups were synthesized by cyclization of the corresponding 1,3-diynes with sodium sulfide or by Suzuki–Miyaura coupling. X-ray analysis and DFT calculations revealed that the molecules adopt nonplanar conformations depending on the steric demand of the anthryl groups. The dihedral angles between the arene units are an important contributor to the photophysical properties in the electronic spectra as well as the electrochemical data.

[1]  Haifeng Cheng,et al.  Synthesis, characterizations and electrochromic properties of polymers based on functionalized anthracene , 2016 .

[2]  F. M. Irudayanathan,et al.  Copper-catalyzed direct synthesis of furans and thiophenes via decarboxylative coupling of alkynyl carboxylic acids with H2O or Na2S , 2015 .

[3]  Lei Zhang,et al.  A general approach to arylated furans, pyrroles, and thiophenes , 2014 .

[4]  Seul-Ong Kim,et al.  Efficient diketopyrrolopyrrole-based small-molecule bulk-heterojunction solar cells with different electron-donating end-groups. , 2014, Chemistry, an Asian journal.

[5]  Linghai Xie,et al.  Highly efficient C–C cross-coupling for installing thiophene rings into π-conjugated systems , 2014 .

[6]  T. Kawakami,et al.  Synthesis of 2,9-Diethynylanthracene Derivatives , 2014 .

[7]  M. Yoshizawa,et al.  Molecular architectures of multi-anthracene assemblies. , 2014, Chemical Society reviews.

[8]  S. Bourgault,et al.  Synthesis of 2,5-diaryl-substituted thiophenes as helical mimetics: towards the modulation of islet amyloid polypeptide (IAPP) amyloid fibril formation and cytotoxicity. , 2014, Chemistry.

[9]  S. Toyota,et al.  Three-dimensional aromatic networks. , 2014, Topics in current chemistry.

[10]  Y. Murata,et al.  Site-selective sequential coupling reactions controlled by "Electrochemical Reaction Site Switching": a straightforward approach to 1,4-bis(diaryl)buta-1,3-diynes. , 2012, Organic & biomolecular chemistry.

[11]  Jialiang Tang,et al.  Synthesis of 2,5-disubstituted thiophenes via metal-free sulfur heterocyclization of 1,3-diynes with sodium hydrosulfide , 2012 .

[12]  W. Zeng,et al.  Copper(I)-catalyzed synthesis of 2,5-disubstituted furans and thiophenes from haloalkynes or 1,3-diynes. , 2012, The Journal of organic chemistry.

[13]  S. Toyota.  Construction of novel molecular architectures from anthracene units and acetylene linkers , 2012 .

[14]  M. Iyoda,et al.  Conjugated macrocycles: concepts and applications. , 2011, Angewandte Chemie.

[15]  T. Müller,et al.  Pseudo five-component synthesis of 2,5-di(hetero)arylthiophenes via a one-pot Sonogashira–Glaser cyclization sequence , 2011, Beilstein journal of organic chemistry.

[16]  R. Tykwinski,et al.  Conjugated Oligomers and Polymers Based on Anthracene, Tetracene, Pentacene, Naphthodithiophene, and Anthradithiophene Building Blocks , 2011 .

[17]  Hsiao-hua Yu,et al.  Efficient synthesis of 3,4-ethylenedioxythiophene (EDOT)-based functional π-conjugated molecules through direct C-H bond arylations. , 2011, Organic letters.

[18]  Jong Min Lim,et al.  Synthesis of carbazole-containing porphyrinoids by a multiple annulation strategy: a core-modified and π-expanded porphyrin. , 2011, Angewandte Chemie.

[19]  K. Miyashita,et al.  Synthesis and evaluation of novel 3,4-epoxypiperidines as efficient DNA alkylating agents , 2010 .

[20]  G. Nienhaus,et al.  Anthracene-BODIPY dyads as fluorescent sensors for biocatalytic Diels-Alder reactions. , 2010, Journal of the American Chemical Society.

[21]  M. Iyoda,et al.  Supramolecular Structures and Nanoassemblies of Oligothiophenes and Tetrathiafulvalenes , 2011 .

[22]  M. Schiek,et al.  Self-Organized Growth of Organic Thiophene−Phenylene Nanowires on Silicate Surfaces , 2009 .

[23]  Igor F. Perepichka,et al.  Handbook of Thiophene-Based Materials , 2009 .

[24]  甲 千寿子,et al.  単結晶構造解析ソフトウェア（Yadokari-XG 2009）の公開 , 2009 .

[25]  Chang-Qi Ma,et al.  Functional oligothiophenes: molecular design for multidimensional nanoarchitectures and their applications. , 2009, Chemical reviews.

[26]  G. Schnakenburg,et al.  Synthesis of FunctionalizedOligophenylenes and Oligoarylenes Bearing Heteroaryl Groups , 2009 .

[27]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[28]  T. Tilley,et al.  9,10-Dichlorooctafluoroanthracene as a building block for n-type organic semiconductors. , 2007, The Journal of organic chemistry.

[29]  Y. Tobe,et al.  Molecular loops and belts. , 2006, Chemical reviews.

[30]  T. Ikeda,et al.  Syntheses and properties of donor-acceptor-type 2,5-diarylthiophene and 2,5-diarylthiazole. , 2004, Organic letters.

[31]  Wen‐Bin Zhang,et al.  Star-shaped polycyclic aromatics based on oligothiophene-functionalized truxene: synthesis, properties, and facile emissive wavelength tuning. , 2003, Journal of the American Chemical Society.

[32]  C. Näther,et al.  Pyrolysis of a tubular aromatic compound. , 2003, Organic letters.

[33]  Kaname Ito,et al.  Oligo(2,6-anthrylene)s: acene-oligomer approach for organic field-effect transistors. , 2003, Angewandte Chemie.

[34]  Y. Aso,et al.  Functional oligothiophenes as advanced molecular electronic materials , 2002 .

[35]  Y. Tobe,et al.  Synthesis of butadiyne-bridged [4n] metacyclophanes having exo-annular t-butyl groups , 2001 .

[36]  M. Ōki,et al.  Rotational Isomerism Involving an Acetylenic Carbon: Synthesis of and Barrier to Rotation around C(sp)-C(sp3) Bonds in Bis(1,4-disubstituted 9-triptycyl)ethynes , 2000 .

[37]  Y. Yoshida,et al.  Phenyl-capped oligothiophenes: novel light-emitting materials with different molecular alignments in thin films , 1999 .

[38]  D. Burton,et al.  A FACILE SYNTHESIS OF DIYNES , 1997 .

[39]  S. Akiyama,et al.  The Preparation of 9-Ethynylanthracene and 9-Ethynyltriptycene and Their Oxidative Coupling , 1971 .

[40]  S. Akiyama,et al.  Cyclic Acetylenes. VIII. Synthesis of 1, 1′-Dianthryltetraacetylene. A Model Substance of a Cyclic Octaacetylene Containing Anthracene Nuclei , 1960 .