Skip to main content
SpringerLink
Log in
Book cover

Helicene Chemistry pp 153–184Cite as

Reactivity and Transformations

  • Chapter
  • First Online:

  • 1378 Accesses

Abstract

This chapter describes the reactions and transformations of helicenes, which are classified into four sections. First, transformation of the helical skeletons is discussed. By intramolecular Diels–Alder reaction, unusual [2+2] cycloaddition of C=C double bonds on the terminal rings, and dioxygen-triggered transannular dearomatization of helicene, some unprecedented reaction products can be obtained. The second section describes the direct C–H functionalization, which provides the most useful method for modification of the helicene structures. Functionalization of helicenes can be easily achieved by electrophilic aromatic substitution including nitration, halogenation, and acylation. For heterohelicenes, some C–H bonds can be activated by themselves, while the functionalizations of helicenium cation and azahelicenes are also shown. In third section, the transformations of bromohelicenes and hydroxyl helicenes are introduced, which can conveniently produce various functionalized helicene derivatives. Finally, recent advances in the preparation of helicene-embedded organometallics are discussed. When two Cp rings are embedded into the termini of the helicene skeleton, helical metallocene or polymeric metallocene can be obtained. With helicenes as monodentate ligands, bidentate ligands, or multitopic ligands, various metal complexes of helicenes and metallahelicenes are produced, and they exhibit the enhanced chiroptical properties of helicene core, redox switching, and acid–base switching phenomena, and even the acid/base-triggered switch of circularly polarized luminescence. Moreover, they are also potential candidates for the application of asymmetric synthesis.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   99.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   129.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD   129.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

References

  1. Martin RH, Jespers J, Defay N (1975) 1-Hydroxymethyl[6]Helicene—Acid-Catalyzed intramolecular rearrangement involving Helicene Skeleton. Tetrahedron Lett 13:1093–1096

    Article  Google Scholar 

  2. Jespers J, Defay N, Martin RH (1977) Helicenes—Intramolecular insertion reaction involving Helicene Skeleton. Tetrahedron 33(16):2141–2142

    Article  CAS  Google Scholar 

  3. Fuchter MJ, Weimar M, Yang X, Judge DK, White AJP (2012) An unusual oxidative rearrangement of [7]-helicene. Tetrahedron Lett 53(9):1108–1111

    Article  CAS  Google Scholar 

  4. Berger RJF, Fuchter MJ, Krossing I, Rzepa HS, Schaefer J, Scherer H (2014) Gold(I) mediated rearrangement of [7]-helicene to give a benzo[cd]pyrenium cation embedded in a chiral framework. Chem Commun (Camb) 50(40):5251–5253

    Article  CAS  Google Scholar 

  5. Martin RH, Jespers J, Defay N (1975) Helicenes—Thermally induced intramolecular 4+2 Cycloadditions involving [6]Helicene Skeleton. Helv Chim Acta 58(3):776–779

    Article  CAS  Google Scholar 

  6. Wang DZ, Katz TJ, Golen J, Rheingold AL (2004) Diels-Alder additions of benzynes within helicene skeletons. J Org Chem 69(22):7769–7771

    Article  CAS  Google Scholar 

  7. Garcia MH, Florindo P, Piedade MDM, Maiorana S, Licandro E (2009) New organometallic Ru(II) and Fe(II) complexes with tetrathia-[7]-helicene derivative ligands. Polyhedron 28(3):621–629

    Article  CAS  Google Scholar 

  8. Yavari K, Moussa S, Ben Hassine B, Retailleau P, Voituriez A, Marinetti A (2012) 1H-Phosphindoles as structural units in the synthesis of Chiral Helicenes. Angew Chem Int Ed 51(27):6748–6752

    Google Scholar 

  9. Sakai H, Shinto S, Kumar J, Araki Y, Sakanoue T, Takenobu T, Wada T, Kawai T, Hasobe T (2015) Highly Fluorescent [7]Carbohelicene Fused by Asymmetric 1,2-Dialkyl-Substituted Quinoxaline for Circularly Polarized Luminescence and Electroluminescence. J Phys Chem C 119(24):13937–13947

    Google Scholar 

  10. Shen Y, Lu H-Y, Chen C-F (2014) Dioxygen-Triggered Transannular Dearomatization of Benzo[5]helicene Diols: highly efficient synthesis of Chiral π-Extended Diones. Angew Chem Int Ed 53(18):4648–4651

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  12. Chen JD, Lu HY, Chen CF (2010) Synthesis and structures of Multifunctionalized Helicenes and Dehydrohelicenes: an efficient route to construct cyan fluorescent molecules. Chem Eur J 16(39):11843–11846

    Article  CAS  Google Scholar 

  13. Nakano K, Hidehira Y, Takahashi K, Hiyama T, Nozaki K (2005) Stereospecific synthesis of hetero[7]helicenes by Pd-catalyzed double N-arylation and intramolecular O-arylation. Angew Chem Int Ed 44(43):7136–7138

    Article  CAS  Google Scholar 

  14. Dai YJ, Katz TJ (1997) Synthesis of helical conjugated ladder polymers. J Org Chem 62(5):1274–1285

    Article  CAS  Google Scholar 

  15. Shi SH, Katz TJ, Yang BWV, Liu LB (1995) Use of Thiazyl Chlorides, Alkyl Carbamates, and Thionyl Chloride to Fuse 1,2,5-Thiadiazoles to Quinones and to Oxidize, Chlorinate, and Aminate Them. J Org Chem 60(5):1285–1297

    Article  CAS  Google Scholar 

  16. Maiorana S, Papagni A, Licandro E, Annunziata R, Paravidino P, Perdicchia D, Giannini C, Bencini M, Clays K, Persoons A (2003) A convenient procedure for the synthesis of tetrathia-[7]-helicene and the selective alpha-functionalisation of terminal thiophene ring. Tetrahedron 59(34):6481–6488

    Article  CAS  Google Scholar 

  17. Doulcet J, Stephenson GR (2015) Novel asymmetric formylation of aromatic compounds: enantioselective synthesis of formyl 7,8-Dipropyltetrathia[7]helicenes. Chem Eur J 21(38):13431–13436

    Article  CAS  Google Scholar 

  18. Torricelli F, Bosson J, Besnard C, Chekini M, Bürgi T, Lacour J (2013) Modular synthesis, orthogonal post-functionalization, absorption, and Chiroptical properties of cationic [6]Helicenes. Angew Chem Int Ed 52(6):1796–1800

    Article  CAS  Google Scholar 

  19. 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 

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

    Article  Google Scholar 

  21. Takenaka N, Chen JS, Captain B, Sarangthem RS, Chandrakumar A (2010) Helical Chiral 2-Aminopyridinium Ions: a new class of hydrogen bond donor catalysts. J Am Chem Soc 132(13):4536–4537

    Article  CAS  Google Scholar 

  22. Chen J, Captain B, Takenaka N (2011) Helical Chiral 2,2′-Bipyridine N-Monoxides as Catalysts in the Enantioselective Propargylation of Aldehydes with Allenyltrichlorosilane. Org Lett 13(7):1654–1657

    Article  CAS  Google Scholar 

  23. Kaneko E, Matsumoto Y, Kamikawa K (2013) Synthesis of Azahelicene N-Oxide by Palladium-Catalyzed Direct C–H Annulation of a Pendant (Z)-Bromovinyl Side Chain. Chem Eur J 19(36):11837–11841

    Article  CAS  Google Scholar 

  24. Dova D, Cauteruccio S, Prager S, Dreuw A, Graiff C, Licandro E (2015) Chiral Thiahelicene-Based Alkyl Phosphine-Borane Complexes: Synthesis, X-ray Characterization, and Theoretical and Experimental Investigations of Optical Properties. J Org Chem 80(8):3921–3928

    Article  CAS  Google Scholar 

  25. Liu LB, Katz TJ (1991) Bromine Auxiliaries in Photosyntheses of [5]Helicenes. Tetrahedron Lett 32(47):6831–6834

    Article  CAS  Google Scholar 

  26. Tinnemans AHA, Laarhoven WH, Sharafiozeri S, Muszkat KA (1975) Photodehydrocyclizations of stilbene-like compounds. 15. Electronic overlap population as a reactivity measure in Photocyclizations of Pentahelicenes. Recueil Des Travaux Chimiques Des Pays-Bas 94(11):239–243

    Google Scholar 

  27. Frimer AA, Kinder JD, Youngs WJ, Meador MAB (1995) Reinvestigation of the Photocyclization of 1,4-Phenylene Bis(Phenylmaleic Anhydride)—Preparation and Structure of [5]Helicene 5,6-9,10-Dianhydride. J Org Chem 60(6):1658–1664

    Article  CAS  Google Scholar 

  28. Ito N, Hirose T, Matsuda K (2014) Facile photochemical synthesis of 5,10-Disubstituted [5]Helicenes by removing molecular orbital degeneracy. Org Lett 16(9):2502–2505

    Article  CAS  Google Scholar 

  29. Yamamoto K, Sonobe H, Matsubara H, Sato M, Okamoto S, Kitaura K (1996) Convenient new synthesis of [7]circulene. Angew Chem Int Ed Engl 35(1):69–70

    Article  Google Scholar 

  30. Shimizu M, Nagao I, Tomioka Y, Hiyama T (2008) Palladium-Catalyzed Annulation of vic-Bis(pinacolatoboryl)alkenes and -phenanthrenes with 2,2′-Dibromobiaryls: facile synthesis of functionalized Phenanthrenes and Dibenzo[g, p]chrysenes. Angew Chem Int Ed 47(42):8096–8099

    Article  CAS  Google Scholar 

  31. Groen MB, Schadenb H, Wynberg H (1971) Synthesis and resolution of some heterohelicenes. J Org Chem 36(19):2797–2809

    Google Scholar 

  32. Dopper JH, Oudman D, Wynberg H (1973) Use of Thieno[2,3-B]Thiophene in Synthesis of Heterohelicenes by Double Photocyclizations. J Am Chem Soc 95(11):3692–3698

    Article  CAS  Google Scholar 

  33. Dopper JH, Oudman D, Wynberg H (1975) Dehydrogenation of Heterohelicenes by a scholl type reaction—Dehydrohelicenes. J Org Chem 40(23):3398–3401

    Article  CAS  Google Scholar 

  34. Tinnemans AHA, Laarhoven WH (1974) Photodehydrocyclizations in stilbene-like compounds. IX. 1,2-Phenyl shifts in the cyclization of 1-phenylpentahelicenes. J Am Chem Soc 96(14):4611–4616

    Article  CAS  Google Scholar 

  35. Rajca A, Miyasaka M, Xiao SZ, Boratynski PJ, Pink M, Rajca S (2009) Intramolecular cyclization of thiophene-based [7]Helicenes to Quasi-[8]Circulenes. J Org Chem 74(23):9105–9111

    Article  CAS  Google Scholar 

  36. Rajca A, Pink M, Xiao SZ, Miyasaka M, Rajca S, Das K, Plessel K (2009) Functionalized thiophene-based [7]Helicene: Chirooptical properties versus electron delocalization. J Org Chem 74(19):7504–7513

    Article  CAS  Google Scholar 

  37. Žádný J, Velíšek P, Jakubec M, Sýkora J, Církva V, Storch J (2013) Exploration of 9-bromo[7]helicene reactivity. Tetrahedron 69(30):6213–6218

    Article  Google Scholar 

  38. Goretta S, Tasciotti C, Mathieu S, Smet M, Maes W, Chabre YM, Dehaen W, Giasson R, Raimundo JM, Henry CR, Barth C, Gingras M (2009) Expeditive syntheses of functionalized Pentahelicenes and NC-AFM on Ag(001). Org Lett 11(17):3846–3849

    Article  CAS  Google Scholar 

  39. Songis O, Misek J, Schmid MB, Kollarovie A, Stara IG, Saman D, Cisarova I, Stary I (2010) A versatile synthesis of functionalized pentahelicenes. J Org Chem 75(20):6889–6899

    Article  CAS  Google Scholar 

  40. Moussa S, Aloui F, Hassine BB (2013) Synthesis and characterization of a new chiral pentacyclic phosphine. Synth Commun 43(2):268–276

    Article  CAS  Google Scholar 

  41. Yamamoto K, Ikeda T, Kitsuki T, Okamoto Y, Chikamatsu H, Nakazaki M (1990) Synthesis and chiral recognition of optically-active crown ethers incorporating a Helicene moiety as the chiral center. J Chem Soc Perkin Trans 1(2):271–276

    Article  Google Scholar 

  42. Paruch K, Vyklicky L, Wang DZ, Katz TJ, Incarvito C, Zakharov L, Rheingold AL (2003) Functionalizations of [6]- and [7]Helicenes at their most sterically hindered positions. J Org Chem 68(22):8539–8544

    Article  CAS  Google Scholar 

  43. Biet T, Fihey A, Cauchy T, Vanthuyne N, Roussel C, Crassous J, Avarvari N (2013) Ethylenedithio-Tetrathiafulvalene-Helicenes: Electroactive Helical Precursors with Switchable Chiroptical Properties. Chem Eur J 19(39):13160–13167

    Article  CAS  Google Scholar 

  44. Teply F, Stara IG, Stary I, Kollarovic A, Saman D, Vyskocil S, Fiedler P (2003) Synthesis of 3-hexahelicenol and its transformation to 3-hexahelicenylamines, diphenylphosphine, methyl carboxylate, and dimethylthiocarbamate. J Org Chem 68(13):5193–5197

    Article  CAS  Google Scholar 

  45. Weimar M, Correa da Costa R, Lee F-H, Fuchter MJ (2013) A scalable and expedient route to 1-Aza[6]Helicene derivatives and its subsequent application to a chiral-relay asymmetric strategy. Org Lett 15(7):1706–1709

    Article  CAS  Google Scholar 

  46. Thomson PF, Parrish D, Pradhan P, Lakshman MK (2015) Modular, Metal-Catalyzed Cycloisomerization approach to angularly fused Polycyclic Aromatic Hydrocarbons and Their Oxidized Derivatives. J Org Chem 80(15):7435–7446

    Article  CAS  Google Scholar 

  47. Usui K, Yamamoto K, Shimizu T, Okazumi M, Mei B, Demizu Y, Kurihara M, Suemune H (2015) Synthesis and resolution of substituted [5]Carbohelicenes. J Org Chem 80(12):6502–6508

    Article  CAS  Google Scholar 

  48. Schweinfurth D, Zalibera M, Kathan M, Shen C, Mazzolini M, Trapp N, Crassous J, Gescheidt G, Diederich F (2014) Helicene Quinones: Redox-Triggered Chiroptical switching and chiral recognition of the semiquinone radical anion lithium salt by electron nuclear double resonance spectroscopy. J Am Chem Soc 136(37):13045–13052

    Article  CAS  Google Scholar 

  49. Dreher SD, Katz TJ, Lam KC, Rheingold AL (2000) Application of the Russig-Laatsch reaction to synthesize a bis[5]Helicene chiral pocket for asymmetric catalysis. J Org Chem 65(3):815–822

    Article  CAS  Google Scholar 

  50. Nakano D, Hirano R, Yamaguchi M, Kabuto C (2003) Synthesis of optically active bihelicenols. Tetrahedron Lett 44(18):3683–3686

    Article  CAS  Google Scholar 

  51. Hrbac J, Storch J, Halouzka V, Cirkva V, Matejka P, Vacek J (2014) Immobilization of Helicene onto carbon substrates through electropolymerization of [7]helicenyl-thiophene. RSC Advances 4(86):46102–46105

    Article  CAS  Google Scholar 

  52. Katz TJ, Slusarek W (1979) Helical Hydrocarbons Capped by 5-Membered Rings as Precursors of Polymeric Metallocenes. J Am Chem Soc 101(15):4259–4267

    Article  CAS  Google Scholar 

  53. Katz TJ, Pesti J (1982) Synthesis of a helical ferrocene. J Am Chem Soc 104(1):346–347

    Article  CAS  Google Scholar 

  54. Sudhakar A, Katz TJ (1986) Asymmetric-Synthesis of helical metallocenes. J Am Chem Soc 108(1):179–181

    Article  CAS  Google Scholar 

  55. Sudhakar A, Katz TJ, Yang BW (1986) Synthesis of a helical Metallocene oligomer. J Am Chem Soc 108(10):2790–2791

    Article  CAS  Google Scholar 

  56. Gilbert AM, Katz TJ, Geiger WE, Robben MP, Rheingold AL (1993) Synthesis and properties of an optically-active helical bis-cobaltocenium ion. J Am Chem Soc 115(8):3199–3211

    Article  CAS  Google Scholar 

  57. Katz TJ, Sudhakar A, Teasley MF, Gilbert AM, Geiger WE, Robben MP, Wuensch M, Ward MD (1993) Synthesis and properties of optically-active helical Metallocene Oligomers. J Am Chem Soc 115(8):3182–3198

    Article  CAS  Google Scholar 

  58. Malaba D, Djebli A, Chen L, Zarate EA, Tessier CA, Youngs WJ (1993) Lithium-Induced Cyclization of Tribenzocyclyne—synthesis and structural characterization of a novel Helicene Dianion, Its protonated form, Silylated Isomers of a substituted Fulvalene ligand, and a novel dimeric lithium complex. Organometallics 12(4):1266–1276

    Article  CAS  Google Scholar 

  59. Pammer F, Sun Y, Pagels M, Weismann D, Sitzmann H, Thiel WR (2008) Dibenzo[c, g]fluorenyliron: an organometallic relative of pentahelicene. Angew Chem Int Ed 47(17):3271–3274

    Article  CAS  Google Scholar 

  60. Álvarez CM, Barbero H, García-Escudero LA, Martín-Alvarez JM, Martínez-Pérez C, Miguel D (2012) η6-Hexahelicene Complexes of Iridium and Ruthenium: running along the Helix. Inorg Chem 51(15):8103–8111

    Article  Google Scholar 

  61. Rose-Munch F, Li M, Rose E, Daran JC, Bossi A, Licandro E, Mussini PR (2012) Tetrathia[7]helicene-Based complexes of ferrocene and (η5-Cyclohexadienyl)tricarbonylmanganese: synthesis and electrochemical studies. Organometallics 31(1):92–104

    Article  CAS  Google Scholar 

  62. El Abed R, Aloui F, Genet JP, Ben Hassine B, Marinetti A (2007) Synthesis and resolution of 2-(diphenylphosphino)heptahelicene. J Organomet Chem 692(5):1156–1160

    Article  Google Scholar 

  63. Aloui F, Hassine BB (2009) An alternative approach to 3-(diphenylphosphino)hexahelicene. Tetrahedron Lett 50(30):4321–4323

    Article  CAS  Google Scholar 

  64. Yavari K, Aillard P, Zhang Y, Nuter F, Retailleau P, Voituriez A, Marinetti A (2014) Helicenes with embedded Phosphole units in enantioselective gold catalysis. Angew Chem Int Ed 53(3):861–865

    Article  CAS  Google Scholar 

  65. El Sayed Moussa M, Guillois K, Shen W, Réau R, Crassous J, Lescop C (2014) Dissymmetrical U-Shaped π-Stacked supramolecular assemblies by using a Dinuclear CuI Clip with Organophosphorus ligands and Monotopic Fully π-Conjugated Ligands. Chem Eur J 20(45):14853–14867

    Google Scholar 

  66. Misek J, Teply F, Stara IG, Tichy M, Saman D, Cisarova I, Vojtisek P, Stary I (2008) A straightforward route to helically chiral N-heteroaromatic compounds: Practical synthesis of racemic 1,14-diaza[5]helicene and optically pure 1-and 2-aza[6]helicenes. Angew Chem Int Ed 47(17):3188–3191

    Article  CAS  Google Scholar 

  67. Mendola D, Saleh N, Vanthuyne N, Roussel C, Toupet L, Castiglione F, Caronna T, Mele A, Crassous J (2014) Aza[6]helicene platinum complexes: chirality control of cis–trans Isomerism. Angew Chem Int Ed 53(23):5786–5790

    Article  CAS  Google Scholar 

  68. Anger E, Srebro M, Vanthuyne N, Toupet L, Rigaut S, Roussel C, Autschbach J, Crassous J, Réau R (2012) Ruthenium-vinylhelicenes: remote metal-based enhancement and redox switching of the Chiroptical properties of a Helicene Core. J Am Chem Soc 134(38):15628–15631

    Article  CAS  Google Scholar 

  69. Anger E, Srebro M, Vanthuyne N, Roussel C, Toupet L, Autschbach J, Reau R, Crassous J (2014) Helicene-grafted vinyl- and Carbene-osmium complexes: an example of acid-base Chiroptical switching. Chem Commun (Camb) 50(22):2854–2856

    Article  CAS  Google Scholar 

  70. Srebro M, Anger E, Moore Ii B, Vanthuyne N, Roussel C, Réau R, Autschbach J, Crassous J (2015) Ruthenium-Grafted Vinylhelicenes: Chiroptical Properties and redox switching. Chem Eur J 21(47):17100–17115

    Article  CAS  Google Scholar 

  71. 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 

  72. Graule S, Rudolph M, Vanthuyne N, Autschbach J, Roussel C, Crassous J, Reau R (2009) Metal-Bis(helicene) assemblies incorporating pi-Conjugated Phosphole-Azahelicene ligands: impacting Chiroptical properties by metal variation. J Am Chem Soc 131(9):3183

    Article  CAS  Google Scholar 

  73. Graule S, Rudolph M, Shen WT, Williams JAG, Lescop C, Autschbach J, Crassous J, Reau R (2010) Assembly of pi-Conjugated Phosphole Azahelicene derivatives into chiral coordination complexes: an experimental and theoretical study. Chem Eur J 16(20):5976–6005

    Article  CAS  Google Scholar 

  74. Norel L, Rudolph M, Vanthuyne N, Williams JAG, Lescop C, Roussel C, Autschbach J, Crassous J, Reau R (2010) Metallahelicenes: easily accessible Helicene derivatives with large and tunable Chiroptical properties. Angew Chem Int Ed 49(1):99–102

    Article  CAS  Google Scholar 

  75. Anger E, Rudolph M, Shen C, Vanthuyne N, Toupet L, Roussel C, Autschbach J, Crassous J, Réau R (2011) From Hetero- to Homochiral Bis(metallahelicene)s Based on a PtIII−PtIII bonded scaffold: isomerization, structure, and Chiroptical Properties. J Am Chem Soc 133(11):3800–3803

    Article  CAS  Google Scholar 

  76. Shen C, Anger E, Srebro M, Vanthuyne N, Toupet L, Roussel C, Autschbach J, Réau R, Crassous J (2013) Diastereo- and enantioselective synthesis of organometallic Bis(helicene)s by a combination of C–H activation and dynamic isomerization. Chem Eur J 19(49):16722–16728

    Article  CAS  Google Scholar 

  77. Shen C, Anger E, Srebro M, Vanthuyne N, Deol KK, Jefferson TD, Muller G, Williams JAG, Toupet L, Roussel C, Autschbach J, Reau R, Crassous J (2014) Straightforward access to mono- and bis-cycloplatinated Helicenes displaying circularly polarized phosphorescence by using crystallization resolution methods. Chem Sci 5(5):1915–1927

    Article  CAS  Google Scholar 

  78. Saleh N, Moore B, Srebro M, Vanthuyne N, Toupet L, Williams JAG, Roussel C, Deol KK, Muller G, Autschbach J, Crassous J (2015) Acid/Base-Triggered switching of circularly polarized luminescence and electronic circular dichroism in organic and organometallic Helicenes. Chem Eur J 21(4):1673–1681

    Article  CAS  Google Scholar 

  79. Saleh N, Srebro M, Reynaldo T, Vanthuyne N, Toupet L, Chang VY, Muller G, Williams JAG, Roussel C, Autschbach J, Crassous J (2015) Enantio-Enriched CPL-active helicene-bipyridine-rhenium complexes. Chem Commun (Camb) 51(18):3754–3757

    Article  CAS  Google Scholar 

  80. Crespo O, Eguillor B, Esteruelas MA, Fernandez I, Garcia-Raboso J, Gomez-Gallego M, Martin-Ortiz M, Olivan M, Sierra MA (2012) Synthesis and characterisation of [6]-azaosmahelicenes: the first d4-heterometallahelicenes. Chem Commun (Camb) 48(43):5328–5330

    Article  CAS  Google Scholar 

  81. Cauteruccio S, Loos A, Bossi A, Blanco Jaimes MC, Dova D, Rominger F, Prager S, Dreuw A, Licandro E, Hashmi ASK (2013) Gold(I) complexes of Tetrathiaheterohelicene Phosphanes. Inorg Chem 52(14):7995–8004

    Article  CAS  Google Scholar 

  82. Fuchter MJ, Schaefer J, Judge DK, Wardzinski B, Weimar M, Krossing I (2012) [7]-Helicene: a chiral molecular tweezer for silver(i) salts. Dalton Trans 41(27):8238–8241

    Article  CAS  Google Scholar 

  83. Klepetářová B, Makrlík E, Dytrtová JJ, Böhm S, Vaňura P, Storch J (2015) [6]Helicene as a novel molecular tweezer for the univalent silver cation: Experimental and theoretical study. J Mol Struct 1097:124–128

    Article  Google Scholar 

  84. 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 

  85. Fox JM, Katz TJ, Van Elshocht S, Verbiest T, Kauranen M, Persoons A, Thongpanchang T, Krauss T, Brus L (1999) Synthesis, self-assembly, and nonlinear optical properties of conjugated helical metal phthalocyanine derivatives. J Am Chem Soc 121(14):3453–3459

    Article  CAS  Google Scholar 

  86. Sooksimuang T, Mandal BK (2003) [5]Helicene-fused phthalocyanine derivatives. New members of the phthalocyanine family. J Org Chem 68(2):652–655

    Article  CAS  Google Scholar 

  87. Chen LX, Shaw GB, Tiede DM, Zuo XB, Zapol P, Redfern PC, Curtiss LA, Sooksimuang T, Mandal BK (2005) Excited state dynamics and structures of functionalized phthalocyanines. 1. Self-regulated assembly of zinc helicenocyanine. J Phys Chem B 109(35):16598–16609

    Article  CAS  Google Scholar 

  88. Aranda Perez AI, Biet T, Graule S, Agou T, Lescop C, Branda NR, Crassous J, Réau R (2011) Chiral and Extended π-Conjugated Bis(2-pyridyl)phospholes as Assembling N,P,N Pincers for Coordination-Driven synthesis of supramolecular [2,2]Paracyclophane analogues. Chem Eur J 17(4):1337–1351

    Google Scholar 

  89. Vreshch V, El Sayed Moussa M, Nohra B, Srebro M, Vanthuyne N, Roussel C, Autschbach J, Crassous J, Lescop C, Réau R (2013) Assembly of Helicene-Capped N,P,N,P,N-Helicands within CuI Helicates: Impacting Chiroptical Properties by Ligand–Ligand Charge Transfer. Angew Chem Int Ed 52(7):1968–1972

    Google Scholar 

Download references

Author information

Authors and Affiliations

  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

Authors
  1. Chuan-Feng Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yun Shen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chuan-Feng Chen .

Rights and permissions

Reprints and permissions

Copyright information

© 2017 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Chen, CF., Shen, Y. (2017). Reactivity and Transformations. In: Helicene Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-53168-6_8

Download citation

Publish with us

Policies and ethics

Search

Navigation