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Introduction to Helicene Chemistry

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Abstract

In this chapter, a brief introduction to helical structure and helicene is first given followed by the nomenclature. The historical development is discussed in detail, and some landmarks such as the first reported helicene, the demonstration of helical structure by X-ray analysis, the first large-scale synthesis by Diels-Alder addition, and the contributions of leading research groups at different times are highlighted. This book is aimed to become a primer for beginners who want to enter this area and also a useful manual for researchers and graduate students. Literatures from 2012 to early 2016 are covered and important discoveries before 2012 are emphasized as well. At last, helicene-related books or review articles published before 2016 are summarized. If readers are interested in a specific topic, more details could be obtained from them.

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References

  1. Jones KG (1991) Messier’s nebulae and star clusters, 2nd edn. Cambridge University Press, Cambridge

    Google Scholar 

  2. A galactic sunflower. http://www.spacetelescope.org/images/potw1536a/. Accessed 21 Oct 2015

  3. Newman MS, Lednicer D (1956) The synthesis and resolution of hexahelicene. J Am Chem Soc 78(18):4765–4770

    Article  CAS  Google Scholar 

  4. Martin RH (1974) Helicenes. Angew Chem Int Ed Engl 13(10):649–659

    Article  Google Scholar 

  5. Kawazura H, K-i Yamada (1976) Chemistry of heterohelicenes. J Synth Org Chem Jpn 34(2):111–117

    Article  CAS  Google Scholar 

  6. Laarhoven WH, Prinsen WJC (1984) Carbohelicenes and heterohelicenes. Top Curr Chem 125:63–130

    Article  CAS  Google Scholar 

  7. Shen Y, Chen C-F (2012) Helicenes: synthesis and applications. Chem Rev 112(3):1463–1535

    Article  CAS  Google Scholar 

  8. Gingras M (2013) One hundred years of helicene chemistry. Part 3: applications and properties of carbohelicenes. Chem Soc Rev 42(3):1051–1095

    Article  CAS  Google Scholar 

  9. Gingras M (2013) One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes. Chem Soc Rev 42(3):968–1006

    Article  CAS  Google Scholar 

  10. Gingras M, Felix G, Peresutti R (2013) One hundred years of helicene chemistry. Part 2: stereoselective syntheses and chiral separations of carbohelicenes. Chem Soc Rev 42(3):1007–1050

    Article  CAS  Google Scholar 

  11. Wynberg H (1971) Some observations on chemical, photochemical, and spectral properties of thiophenes. Acc Chem Res 4(2):65–73

    Article  CAS  Google Scholar 

  12. Dumitrascu F, Dumitrescu DG, Aronb I (2010) Azahelicenes and other similar tri and tetracyclic helical molecules. Arkivoc 1:1–32

    Google Scholar 

  13. Sato K, Arai S (2002) Cyclophane chemistry for the 21st century. Research Signpost, Kerala

    Google Scholar 

  14. Ghasemabadi PG, Yao T, Bodwell GJ (2015) Cyclophanes containing large polycyclic aromatic hydrocarbons. Chem Soc Rev 44(18):6494–6518

    Article  CAS  Google Scholar 

  15. Meisenheimer J, Witte K (1903) Reduction von 2-nitronaphtalin. Ber Dtsch Chem Ges 36(4):4153–4164

    Article  CAS  Google Scholar 

  16. Clar E (1964) Polycyclic hydrocarbons, vol 1, 1st edn. Springer-Verlag, Berlin Heidelberg, London. doi:10.1007/978-3-662-01665-7

  17. Weitzenböck R, Lieb H (1912) Eine neue synthese des chrysens. Monatshefte für Chemie und verwandte Teile anderer Wissenschaften 33(5):549–565

    Article  Google Scholar 

  18. Weitzenböck R, Klingler A (1918) Synthese der isomeren Kohlenwasserstoffe 1, 2–5, 6-dibenzanthracen und 3, 4–5, 6-dibenzphenanthren. Monatshefte für Chemie und verwandte Teile anderer Wissenschaften 39(5):315–323

    Article  Google Scholar 

  19. Newman MS, Joshel LM (1938) A new synthesis of 3,4-benzphenanthrene. J Am Chem Soc 60(2):485–488

    Article  CAS  Google Scholar 

  20. Clar E (1932) Über die Konstitution des perylens; die Synthesen des 2.3, 10.11-Dibenz- und des 1.12-Benz-peryles und Betrachtungen über die Konstitution des Benzanthrons und Phenanthrens (Zur Kenntnis mehrkerniger aromatischer Kohlenwasserstoffe und ihrer Abkömmlinge, XIV. Mitteil.). Ber Dtsch Chem Ges (A and B Series) 65(5):846–859

    Google Scholar 

  21. Cook JW (1931) CCCL.-Polycyclic aromatic hydrocarbons. Part VI. 3: 4-Benzphenanthrene and its quinone. J Chem Soc (Resumed) (0):2524–2528

    Google Scholar 

  22. Hewett CL (1936) 133. Polycyclic aromatic hydrocarbons. Part XIV. A new synthesis of 3: 4-benzphenanthrene. J Chem Soc (Resumed) (0):596–599

    Google Scholar 

  23. Hewett CL (1938) 241. Polycyclic aromatic hydrocarbons. Part XVIII. A general method for the synthesis of 3: 4-benzphenanthrene derivatives. J Chem Soc (Resumed) (0):1286–1291

    Google Scholar 

  24. Hewett CL (1938) 34. Polycyclic aromatic hydrocarbons. Part XVI. 1: 2: 3: 4-Dibenzphenanthrene. J Chem Soc (Resumed) (0):193–196

    Google Scholar 

  25. Hewett CL (1940) 60. Polycyclic aromatic hydrocarbons. Part XXII. J Chem Soc (Resumed) (0):293–303

    Google Scholar 

  26. Szmuszkovicz J, Modest EJ (1948) Condensation of phenylcycloalkenes with maleic anhydride. I. Synthesis of 7-Methoxy-3,4-benzphenanthrene. J Am Chem Soc 70(7):2542–2543

    Article  Google Scholar 

  27. Bachmann WE, Edgerton RO (1940) The synthesis of 3,4-Benzphenanthrene and 1-Methylpyrene. J Am Chem Soc 62(11):2970–2973

    Article  CAS  Google Scholar 

  28. Bergmann F, Szmuszkowicz J (1947) 1,2,3,4-Dibenzphenanthrene and its derivatives. III. Synthesis of 1,2-Dimethyl-3,4-benzphenanthrene1. J Am Chem Soc 69(6):1367–1370

    Article  CAS  Google Scholar 

  29. Beyer H (1938) Über polycyclische systeme, I. Mitteil.: Die Kondensation des chrysens mit bernsteinsäure-anhydrid. Ber Dtsch Chem Ges (A and B Series) 71(4):915–922

    Google Scholar 

  30. Weidlich HA (1938) Synthese kondensierter Rinǵsysteme (I. Mitteil.). Ber Dtsch Chem Ges (A and B Series) 71(6):1203–1209

    Google Scholar 

  31. Fuchs W, Niszel F (1927) Über die Tautomerie der Phenole, IX.: Die Naphtho-carbazol-Bildung aus Naphtholen. Ber Dtsch Chem Ges (A and B Series) 60(1):209–217

    Google Scholar 

  32. Dischendorfer O (1939) Über die Kondensation von Glyoxal und β-Naphthol. Monatsh Chem/Chemical Monthly 73(1):45–56

    Article  Google Scholar 

  33. Newman MS (1940) A new synthesis of coronene. J Am Chem Soc 62:1683–1687

    Article  CAS  Google Scholar 

  34. McIntosh AO, Robertson JM, Vand V (1952) Crystal Structure of 3.4; 5.6 Dibenzphenanthrene. Nature 169(4295):322–323

    Article  CAS  Google Scholar 

  35. Newman MS, Wheatley WB (1948) Optical Activity of the 4,5-Phenanthrene Type—4-(1-Methylbenzo[C]Phenanthryl)-Acetic Acid and 1-Methylbenzo[C]Phenanthrene. J Am Chem Soc 70(5):1913–1916

    Article  CAS  Google Scholar 

  36. Bell F, Waring DH (1949) 567. The symmetrical dianthryls. Part III. J Chem Soc (Resumed) (0):2689–2693

    Google Scholar 

  37. Newman MS, Lutz WB, Lednicer D (1955) A new reagent for resolution by complex formation—the resolution of phenanthro-[3,4-c]phenanthrene. J Am Chem Soc 77(12):3420–3421

    Article  CAS  Google Scholar 

  38. Mallory FB, Mallory CW, Halpern EJ (1966) Paper presented at the first middle atlantic regional meeting of the American Chemical Society, Philadelphia, Pa, Feb. 3

    Google Scholar 

  39. Carruthers W (1967) Photocyclisation of some stilbene analogues. Synthesis of dibenzo[a,l]pyrene. J Chem Soc C: Org (0):1525–1527

    Google Scholar 

  40. Scholz M, Mühlstädt M, Dietz F (1967) Chemie angeregter zustände. I. Mitt. Die richtung der photocyclisierung naphthalinsubstituierter äthylene. Tetrahedron Lett 8(7):665–668

    Article  Google Scholar 

  41. Flammang-Barbieux M, Nasielski J, Martin RH (1967) Synthesis of heptahelicene (1) benzo [c] phenanthro [4, 3-g]phenanthrene. Tetrahedron Lett 8(8):743–744

    Article  Google Scholar 

  42. Laarhove Wh, Brus GJM (1971) Polarographic data and deviations from coplanarity of helicene molecules. J Chem Soc B-Phy Org 7:1433–1434

    Article  Google Scholar 

  43. Martin RH, Baes M (1975) Helicenes—photosyntheses of [11]Helicene, [12]Helicene and [14]Helicene. Tetrahedron 31(17):2135–2137

    Article  CAS  Google Scholar 

  44. Moradpour A, Kagan H, Baes M, Morren G, Martin RH (1975) Photochemistry with circularly polarized light—III: Synthesis of helicenes using bis(arylvinyl) arenes as precursors. Tetrahedron 31(17):2139–2143

    Article  CAS  Google Scholar 

  45. Liu LB, Yang BW, Katz TJ, Poindexter MK (1991) Improved methodology for photocyclization reactions. J Org Chem 56(12):3769–3775

    Article  CAS  Google Scholar 

  46. Liu LB, Katz TJ (1990) Simple preparation of a helical quinone. Tetrahedron Lett 31(28):3983–3986

    Article  CAS  Google Scholar 

  47. Nuckolls C, Katz TJ, Verbiest T, Van Elshocht S, Kuball HG, Kiesewalter S, Lovinger AJ, Persoons A (1998) Circular dichroism and UV-visible absorption spectra of the Langmuir-Blodgett films of an aggregating helicene. J Am Chem Soc 120(34):8656–8660

    Article  CAS  Google Scholar 

  48. Lovinger AJ, Nuckolls C, Katz TJ (1998) Structure and morphology of helicene fibers (vol 120, p 264, 1998). J Am Chem Soc 120(8):1944–1944

    Google Scholar 

  49. Yang Y, da Costa RC, Fuchter MJ, Campbell AJ (2013) Circularly polarized light detection by a chiral organic semiconductor transistor. Nat Photon 7(8):634–638

    Article  CAS  Google Scholar 

  50. Dai YJ, Katz TJ, Nichols DA (1996) Synthesis of a helical conjugated ladder polymer. Angew Chem Int Ed Engl 35(18):2109–2111

    Article  CAS  Google Scholar 

  51. Peng Z, Takenaka N (2013) Applications of helical-chiral pyridines as organocatalysts in asymmetric synthesis. Chem Rec 13(1):28–42

    Article  CAS  Google Scholar 

  52. Narcis MJ, Takenaka N (2014) Helical-chiral small molecules in asymmetric catalysis. Eur J Org Chem 1:21–34

    Article  Google Scholar 

  53. Virieux D, Sevrain N, Ayad T, Pirat J-L (2015) Chapter Two—helical phosphorus derivatives: synthesis and applications. In: Eric FVS, Christopher AR (eds) Advances in heterocyclic chemistry, vol 116. Academic Press, pp 37–83

    Google Scholar 

  54. Aillard P, Voituriez A, Marinetti A (2014) Helicene-like chiral auxiliaries in asymmetric catalysis. Dalton Trans 43(41):15263–15278

    Article  CAS  Google Scholar 

  55. Yamaguchi M, Shigeno M, Saito N, Yamamoto K (2014) Synthesis, double-helix formation, and higher-assembly formation of chiral polycyclic aromatic compounds: conceptual development of polyketide aldol synthesis. Chem Rec 14(1):15–27

    Article  CAS  Google Scholar 

  56. Wigglesworth TJ, Sud D, Norsten TB, Lekhi VS, Branda NR (2005) Chiral discrimination in photochromic helicenes. J Am Chem Soc 127(20):7272–7273

    Article  CAS  Google Scholar 

  57. Fasel R, Parschau M, Ernst KH (2006) Amplification of chirality in two-dimensional enantiomorphous lattices. Nature 439(7075):449–452

    Article  CAS  Google Scholar 

  58. Shinohara K, Sannohe Y, Kaieda S, Tanaka K, Osuga H, Tahara H, Xu Y, Kawase T, Bando T, Sugiyama H (2010) A Chiral Wedge Molecule Inhibits Telomerase Activity. J Am Chem Soc 132(11):3778–3782

    Article  CAS  Google Scholar 

  59. Stará IG, Starý I (2010) Aromatic ring assemblies, polycyclic aromatic hydrocarbons, and conjugated polyenes, vol 45b

    Google Scholar 

  60. Amatore M (2015) Aubert C (2015) recent advances in stereoselective [2+2+2] cycloadditions. Eur J Org Chem 2:265–286

    Article  Google Scholar 

  61. Tanaka K, Kimura Y, Murayama K (2015) Enantioselective helicene synthesis by rhodium-catalyzed [2+2+2] cycloadditions. Bull Chem Soc Jpn 88(3):375–385

    Article  CAS  Google Scholar 

  62. Carreno MC, Hernandez-Sanchez R, Mahugo J, Urbano A (1999) Enantioselective approach to both enantiomers of helical bisquinones. J Org Chem 64(4):1387–1390

    Article  CAS  Google Scholar 

  63. Shen WT, Graule S, Crassous J, Lescop C, Gornitzka H, Reau R (2008) Stereoselective coordination of ditopic phospholyl-azahelicenes: a novel approach towards structural diversity in chiral pi-conjugated assemblies. Chem Commun (Camb) 7:850–852

    Article  Google Scholar 

  64. Mallory FB, Mallory CW (2004) Photocyclization of stilbenes and related molecules. In: Organic Reactions. John Wiley & Sons, Inc.

    Google Scholar 

  65. Vögtle F (1992) Fascinating molecules in organic chemistry

    Google Scholar 

  66. Hopf H (2000) Classics in hydrocarbon chemistry: syntheses, concepts, perspectives. Wiley-VCH, Weinheim

    Google Scholar 

  67. Agenet N, Buisine O, Slowinski F, Gandon V, Aubert C, Malacria M (2004) Cotrimerizations of acetylenic compounds. In: Organic reactions. John Wiley & Sons, Inc.

    Google Scholar 

  68. Rajca A, Miyasaka M (2007) Synthesis and characterization of novel chiral conjugated materials. In: Functional organic materials. Wiley-VCH Verlag GmbH & Co. KGaA, pp 547–581

    Google Scholar 

  69. Wolf C (2007) Dynamic stereochemistry of chiral compounds: principles and applications. RSC, Cambridge

    Google Scholar 

  70. Smith PJ, Liebman JF, Hopf H, Starý I, Stará IG, Halton B (2009) Strained aromatic molecules. In: Strained hydrocarbons. Wiley-VCH Verlag GmbH & Co. KGaA, pp 147–204

    Google Scholar 

  71. Tanaka K (2013) Synthesis of helically chiral aromatic compounds via [2+2+2] cycloaddition. In: Transition-metal-mediated aromatic ring construction. John Wiley & Sons, Inc., pp 281–298

    Google Scholar 

  72. Plutschack M, Correia C, Seeberger P, Gilmore K (2015) Organic photoredox chemistry in flow. In: Topics in organometallic chemistry. Springer Berlin Heidelberg, pp 1–34

    Google Scholar 

  73. Meurer KP, Vogtle F (1985) Helical molecules in organic chemistry. Top Curr Chem 127:1–76

    Article  CAS  Google Scholar 

  74. Oremek G, Seiffert U, Janecka A (1987) Synthesis and properties of helicenes. Chem Ztg 111(2):69–75

    CAS  Google Scholar 

  75. Osuga H, Suzuki H (1994) Carbohelicenes, heterohelicenes and related systems—some aspects of synthesis and reactions. J Synth Org Chem Jpn 52(12):1020–1031

    Article  CAS  Google Scholar 

  76. Grimme S, Harren J, Sobanski A, Vogtle F (1998) Structure/chiroptics relationships of planar chiral and helical molecules. Eur J Org Chem 8:1491–1509

    Article  Google Scholar 

  77. Katz TJ (2000) Syntheses of functionalized and aggregating helical conjugated molecules. Angew Chem Int Ed 39(11):1921–1923

    Article  CAS  Google Scholar 

  78. Urbano A (2003) Recent developments in the synthesis of helicene-like molecules. Angew Chem Int Ed 42(34):3986–3989

    Article  CAS  Google Scholar 

  79. Collins SK, Vachon MP (2006) Unlocking the potential of thiaheterohelicenes: chemical synthesis as the key. Org Biomol Chem 4(13):2518–2524

    Article  CAS  Google Scholar 

  80. Hoffmann N (2008) Photochemical reactions as key steps in organic synthesis. Chem Rev 108(3):1052–1103

    Article  CAS  Google Scholar 

  81. Jørgensen KB (2010) Photochemical oxidative cyclisation of stilbenes and stilbenoids—the mallory-reaction. Molecules 15(6):4334–4358

    Article  Google Scholar 

  82. Dou G-L, Shi D-Q (2011) Advances in the synthesis of helicenes. Chin J Org Chem 31(12):1989–1996

    CAS  Google Scholar 

  83. Jin T, Zhao J, Asao N, Yamamoto Y (2014) Metal-catalyzed annulation reactions for π-conjugated polycycles. Chem Eur J 20(13):3554–3576

    Article  CAS  Google Scholar 

  84. Saleh N, Shen C, Crassous J (2014) Helicene-based transition metal complexes: synthesis properties and applications. Chem Sci 5(10):3680–3694

    Article  CAS  Google Scholar 

  85. Bosson J, Gouin J, Lacour J (2014) Cationic triangulenes and helicenes: synthesis, chemical stability, optical properties and extended applications of these unusual dyes. Chem Soc Rev 43(8):2824–2840

    Article  CAS  Google Scholar 

  86. Hoffmann N (2014) photochemical reactions applied to the synthesis of helicenes and helicene-like compounds. J Photochem Photobio C: Photochem Rev 19:1–19

    Article  CAS  Google Scholar 

  87. Sánchez-Carnerero EM, Agarrabeitia AR, Moreno F, Maroto BL, Muller G, Ortiz MJ, de la Moya S (2015) Circularly Polarized Luminescence from Simple Organic Molecules. Chem Eur J 21(39):13488–13500

    Google Scholar 

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  1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing, China

    Chuan-Feng Chen & Yun Shen

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  1. Chuan-Feng Chen
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  2. Yun Shen
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Correspondence to Chuan-Feng Chen .

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Chen, CF., Shen, Y. (2017). Introduction to Helicene Chemistry. In: Helicene Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-53168-6_1

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