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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 7
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Original Articles

Synthesis, X-Ray Analysis, and Evaluation of the Optoelectronic Properties of a New Thia[6]helicene

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Pages 1010-1018 | Received 27 Sep 2010, Published online: 16 Dec 2011

REFERENCES

  • Martin , R. H. ; Marchant , M.-J. ; Baes , M. Rapid synthesis of hexa- and heptahelicenes . Helv. Chim. Acta 1971 , 54 , 358 – 360 .
  • (a) Katz , T. J. ; Sudhakar , A. ; Teasley , M. F. ; Gilbert , A. M. ; Geiger , W. E. ; Robben , M. P. ; Wuensch , M. ; Ward , M. D. Synthesis and properties of optically active helical metallocene oligomers. J. Am. Chem. Soc. 1993, 115, 3182–3198; (b) Dai , Y. ; Katz , T. J. Synthesis of helical conjugated ladder polymers. J. Org. Chem. 1997, 62, 1274–1285; (c) Fox , J. M. ; Lin , D. ; Itagaki , Y. ; Fujita , T. Synthesis of conjugated helical acetylene-bridged polymers and cyclophanes. J. Org. Chem. 1998, 63, 2031–2038.
  • Fox , J. M. ; Katz , T. J. Conversion of a [6]helicene into an [8]helicene and a helica . J. Org. Chem. 1999 , 64 , 302 – 305 .
  • (a) Tsuneomi , K. ; Kenta , K. ; Emanuela , L. ; Alberto , B. ; Stefano , M. ; Kenso , S. Enantioselective synthesis induced by tetrathia-[7]-helicenes in conjunction with asymmetric autocatalysis . Tetrahedron: Asymmetry 2006 , 17 , 2050 – 2053 ; (b) Reetz , M. T. ; Sostmann , S. 2,15-Dihydroxy-hexahelicene (HELIXOL): Synthesis and use as an enantioselective fluorescent sensor . J. Organomet. Chem. 2000 , 603 , 105 – 109 ; (c) Dreher , S. D. ; Katz , T. J. ; Lam , K. C. ; Rheingold , A. L. Application of the russig laatsch reaction to synthesize a bis[5]helicene chiral pocket for asymmetric catalysis . J. Org. Chem. 2000 , 65 , 815 – 822 ; (d) Okubo , H. ; Yamaguchi , M. ; Kabuto , C. Macrocyclic amides consisting of helical chiral1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylate . J. Org. Chem. 1998 , 63 , 9500 – 9509 ; (e) Reetz , M. T. ; Beuttenmuller , E. W. ; Goddart , R. First enantioselective catalysis using a helical diphosphane . Tetrahedron Lett. 1997 , 38 , 3211 – 3214 .
  • (a) Ben Hassine , B. ; Gorsane , M. ; Geerts-Evrard , F. ; Pecher , J. ; Martin , R. H. ; Castelet , D. Synthèses et synthèses ennthioselectives d'epoxydes derivant du (E)-stilbene et de l'α-methylstilbene par la methode de payne . Bull. Soc. Chim. Belg. 1986 , 95 , 547 – 556 ; (b) Ben Hassine , B. ; Gorsane , M. ; Pecher , J. ; Martin , R. H. Diastereoselective NaBH4 reductions of (dl) α-ketoesters . Bull. Soc. Chim. Belg. 1985 , 94 , 597 – 603 .
  • (a) Tovar , J. D. ; Rose , A. ; Swager , T. M. Functionalizable polycyclic aromatics through oxidative cyclization of pendant thiophenes . J. Am. Chem. Soc. 2002 , 124 , 7762 – 7769 ; (b) Laquindanum , J. G. ; Katz , H. E. ; Lovinger , A. J. Synthesis, morphology, and field-effect mobility of anthradithiophenes . J. Am. Chem. Soc. 1998 , 120 , 664 – 672 .
  • (a) Boorum , M. M. ; Vasilev , Y. V. ; Drewello , T. ; Scott , L. T. Groundwork for a rational synthesis of C60: Cyclodehydrogenation of a C60H30 polyarene . Science 2001 , 294 , 828 – 831 ; (b) Scott , L. T. ; Boorum , M. M. ; McMahon , B. J. ; Hagen , S. ; Mack , J. ; Blank , J. ; Wegner , H. ; de Meijere , A. A rational chemical synthesis of C60 . Science 2002 , 295 , 1500 – 1503 ; (c) Rabideau , P. W. ; Abdourazak , A. H. ; Marcinow , Z. ; Sygula , R. ; Sygula , A. Buckybowls, 2:Toward the total synthesis of buckminsterfullerene (C60): Benz[5,6]-as-indaceno-[3,2,1,8,7-mnopqr]indeno[4,3,2,1-cdef]chrysene . J. Am. Chem. Soc. 1995 , 117 , 6410 – 6411 ; (d) Sygula , A. ; Rabideau , P. W. A practical, large scale synthesis of the cor-annulene system . J. Am. Chem. Soc. 2000 , 122 , 6323 – 6324 .
  • (a) Wynberg , H. Some observations on the chemical, photochemical, and spectral properties of thiophenes . Acc. Chem. Res. 1971 , 4 , 65 – 67 ; (b) Phillips , K. E. S. ; Katz , T. J. ; Jockusch , S. ; Lovinger , A. J. ; Turro , N. J. Synthesis and properties of an aggregating heterocyclic helicene . J. Am. Chem. Soc. 2001 , 123 , 11899 – 11907 ; (c) Kitahara , Y. ; Tanaka , K. Synthesis, crystal structure and properties of thiaheterohelicenes containing phenolic hydroxy functions . Chem. Commun. 2002 , 932 – 933 ; (d) Miyasaka , M. ; Rajca , A. ; Pink , M. ; Rajca , S. Chiral molecular glass: Synthesis and characterization of enantiomerically pure thiophene-based [7]-helicene . Chem. Eur. J. 2004 , 10 , 6531 – 6539 ; (e) Maiorana , S. ; Papagni , A. ; Licandro , E. ; Annunziata , R. ; Paravidino , P. ; Perdicchia , D. ; Giannini , C. ; Bencini , M. ; Clays , K. ; Persoons , A. A convenient procedure for the synthesis of tetrathia-[7]-helicene . Tetrahedron 2003 , 59 , 6481 – 6488 .
  • Caronna , T. ; Sinisi , R. ; Catellani , M. ; Luzzati , S. ; Abbate , S. ; Longhi , G. Chiroptical properties of some monoazapentahelicenes . Synth. Met. 2001 , 119 , 79 – 80 .
  • (a) Tanaka , K. ; Osuga , H.; Suzuki H. Diastereocontrolled synthesis of optically pure functionalized heterohelicenes. Tetrahedron: Asymmetry 1993, 4, 1843–1856; (b) Murguly , E. ; McDonald , R. ; Branda , N. R. Chiral discrimination in hydrogen-bonded [7]helicenes. Org. Lett. 2000, 2, 3169–3172; (c) Stammel , C. ; Fröhlich , R. ; Wolff , C. ; Wenck , H. ; Mattay , J. Efficient phenanthrene, helicene, and azahelicene syntheses. Eur. J. Org. Chem. 1999, 1709–1718.
  • Aloui , F. ; El Abed , R. ; Ben Hassine , B. ; Marinetti , A. A new approach to 3,14-dihydroxyhexahelicene: Resolution and attribution of the absolute configuration . C. R. Chimie 2009 , 12 , 284 – 290 .
  • Sheldrick , M. Program for Crystal Structure Refinement, University of Göttingen ; Germany , 1997 . SHELXL-97:
  • Liu , L. ; Yang , B. ; Katz , T. J. ; Poindexter , M. K. Improved methodology for photocyclization reactions . J. Org. Chem. 1991 , 56 , 3769 – 3775 .
  • Ku , C.-H. ; Kuo , C.-H. ; Leung , M.-K. ; Hsieh , K.-H. Carbazole–oxadiazole containing polyurethanes as phosphorescent host for organic light emitting diodes . Eur. Polym. J. 2009 , 45 , 1545 – 1553 .
  • Phokaa , S. ; Laokul , P. ; Swatsitang , E. ; Promarak , V. ; Seraphinc , S. ; Maensiri , S. Synthesis, structural and optical properties of CeO2 nanoparticles synthesized by a simple polyvinyl pyrrolidone (PVP) solution route . Mater. Chem. Phys. A 2009 , 115 , 423 – 428 .

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