One hundred years of helicene chemistry. Part 3: applications and properties of carbohelicenes.

Carbohelicenes are a class of fascinating chiral helical molecules which have a rich history in chemistry. Over a period of almost 100 years, chemists have developed many methods to prepare them in a racemic or in a non-racemic form. They also possess a series of interesting chiral, physical, electronic and optical properties. However, their utilization in chemistry or chemistry-related fields has rarely appeared in a detailed and comprehensive review. It is the purpose of this review to collect fundamental applications and functions involving carbohelicenes in various disciplines such as in materials science, in nanoscience, in biological chemistry and in supramolecular chemistry. From the numerous synthetic methodologies reported up to now, carbohelicenes and their derivatives can be tailor-made for a better involvement in several subfields. Among those domains are: nanosciences, chemosensing, liquid crystals, molecular switches, polymers, foldamers, supramolecular materials, molecular recognition, conductive and opto-electronic materials, nonlinear optics, chirality studies and asymmetric synthesis. Helicene chemistry is now at a developmental stage, where sufficient application data are now collected and are extremely useful. They provide many more ideas for setting up the basis for future innovative applications.

[1]  T. Ubukata,et al.  Chiral helicenoid diarylethene with highly diastereoselective photocyclization. , 2007, The Journal of organic chemistry.

[2]  J. Fox,et al.  Synthesis of Conjugated Helical Acetylene-Bridged Polymers and Cyclophanes , 1998 .

[3]  K. Soai,et al.  Asymmetric autocatalysis and the origin of chiral homogeneity in organic compounds. , 2001, Chemical record.

[4]  Katz,et al.  Syntheses of Functionalized and Aggregating Helical Conjugated Molecules I thank the US National Science Foundation for support (CHE98-02316). , 2000, Angewandte Chemie.

[5]  T. J. Katz,et al.  Synthesis of Helical Conjugated Ladder Polymers , 1997 .

[6]  R. Fasel,et al.  X-ray Photoelectron Diffraction: Probing Atom Positions and Molecular Orientation at Surfaces , 2002 .

[7]  M. Gingras,et al.  Functionalized heptahelicene bidentate ligands and chiral building blocks , 2005 .

[8]  K. Ernst Aspects of Molecular Chirality at Metal Surfaces , 2009 .

[9]  M. Yamaguchi,et al.  Chiral recognition of an anionic tetrahelicene by native cyclodextrins. Enantioselectivity dominated by location of a hydrophilic group of the guest in a cyclodextrin cavity , 1999 .

[10]  R. Hoffmann,et al.  Learning from molecules in distress. , 2008, Angewandte Chemie.

[11]  L. Chien,et al.  Photo-Asymmetric Synthesis of Helicenes in Liquid Crystals , 1997 .

[12]  K. Soai,et al.  Asymmetric autocatalysis and its application to chiral discrimination. , 2002, Chirality.

[13]  N. Kobayashi Optically active phthalocyanines , 2001 .

[14]  A. Persoons,et al.  Beneficial effect of heating on the morphology and second-order nonlinear optical efficiency of anisotropic thin films , 2000 .

[15]  R. Nolte,et al.  Self-assembly of disk-shaped molecules to coiled-coil aggregates with tunable helicity , 1999, Science.

[16]  K. Fujiwara,et al.  Four-way-output molecular response system based on the dihydrodibenzo[c,g]phenanthrene skeleton : modulation of CD and FDCD activity by acid and electron-transfer , 2008 .

[17]  Karen E. S. Phillips,et al.  Synthesis and properties of an aggregating heterocyclic helicene. , 2001, Journal of the American Chemical Society.

[18]  T. Bender,et al.  Introduction of a [5]Helicene Unit in Polyimides by Chemical and Thermal Transformations of Precursor Polymers , 1997 .

[19]  T. Ross Kelly,et al.  New Molecular Devices: In Search of a Molecular Ratchet , 1998 .

[20]  F. Aloui,et al.  Synthesis and X‐Ray Analysis of a New [6]Helicene , 2006 .

[21]  H. Staab,et al.  Synthesis, structure and ‘proton sponge’ properties of 1,12-bis(dimethylamino)benzo[c]phenanthrene , 1995 .

[22]  Kazuhiko Tanaka,et al.  Clathrate formation by and self-assembled supramolecular structures of a “molecular spring” , 2000 .

[23]  T. B. Norsten,et al.  Chiral discrimination in photochromic helicenes. , 2005, Journal of the American Chemical Society.

[24]  C. Nuckolls,et al.  Structure and Morphology of Helicene Fibers , 1998 .

[25]  G. Gottarelli,et al.  Determination of absolute configuration of helicenes and related biaryls from calculation of helical twisting powers by the surface chirality model , 1999 .

[26]  R. Fasel,et al.  Two-dimensional separation of [7]helicene enantiomers on Cu(111). , 2001, Chirality.

[27]  P. Ihalainen,et al.  Nonlinear optical and structural properties of langmuir-blodgett films of thiohelicenebisquinones. , 2008, The journal of physical chemistry. B.

[28]  T. Ross Kelly,et al.  In Search of Molecular Ratchets , 1997 .

[29]  K. Ernst Supramolecular surface chirality , 2006 .

[30]  Hiroki Sugiura,et al.  Marked effect of aromatic solvent on unfolding rate of helical ethynylhelicene oligomer. , 2004, Journal of the American Chemical Society.

[31]  T. Bender,et al.  Molecular approach to the development of polyimides with novel structures and properties , 2000 .

[32]  Takashi Kawase,et al.  A chiral wedge molecule inhibits telomerase activity. , 2010, Journal of the American Chemical Society.

[33]  T. C. Shami,et al.  Chiral Nanoscience and Nanotechnology , 2008 .

[34]  D. Lednicer,et al.  The Synthesis and Resolution of Hexahelicene1 , 1956 .

[35]  J. Mattay,et al.  Excited state behaviour of pentahelicene dinitriles , 1999 .

[36]  A. Persoons,et al.  Strong enhancement of nonlinear optical properties through supramolecular chirality , 1998, Science.

[37]  Carsten Schmuck,et al.  Molecules with helical structure: how to build a molecular spiral staircase. , 2003, Angewandte Chemie.

[38]  T. J. Katz,et al.  The synthesis of a helical ferrocene , 1982 .

[39]  M. Yamaguchi,et al.  Synthesis of symmetrical polynitrohelicenes and their chiral recognition in the charge transfer complexation. , 2001, The Journal of organic chemistry.

[40]  M. Yamaguchi,et al.  Synthesis and Charge Transfer Complexation of Chiral Polynitrohelicenes , 2000 .

[41]  B. Captain,et al.  Helical chiral pyridine N-oxides: a new family of asymmetric catalysts. , 2008, Angewandte Chemie.

[42]  H. Ikeda,et al.  Multi-input/multi-output molecular response system based on the dynamic redox behavior of 3,3,4,4-tetraaryldihydro[5]helicene derivatives: reversible formation/destruction of chiral fluorophore and modulation of chiroptical properties by solvent polarity. , 2009, Chemistry.

[43]  Lin Pu,et al.  Fluorescence of organic molecules in chiral recognition. , 2004, Chemical reviews.

[44]  Hiroki Sugiura,et al.  Helix-dimer–Random-coil Thermal Switching Process of Ethynylhelicene Heptamer Highly Sensitive to Its Environment , 2007 .

[45]  Béchir Ben Hassine,et al.  Synthèses et Synthèses Enantiosélectives D'Epoxydes Derivant du (E)‐Stilbène et de L'α‐Méthylstyrène Par la Méthode de Payne , 2010 .

[46]  K Yamada,et al.  Chiral recognition of thiaheterohelicenes by alkyl beta-D-pyranoside micelles. Influence of extension of helix. , 2001, Chemical & pharmaceutical bulletin.

[47]  X. Meng,et al.  Synthesis, resolution and racemization study of helically twisted o-terphenyls , 1999 .

[48]  A. Ferrarini,et al.  Chiral doping of nematic phases and its application to the determination of absolute configuration. , 2008, Chirality.

[49]  Hiroki Sugiura,et al.  Functionalized [3 + 3]cycloalkynes: substituent effect on self-aggregation by nonplanar pi-pi interactions. , 2005, The Journal of organic chemistry.

[50]  Samuel H. Gellman,et al.  Foldamers: A Manifesto , 1998 .

[51]  B. K. Mandal,et al.  Synthetic methodology towards novel polyphenylated naphthalocyanines , 2006 .

[52]  H. L. Carrell,et al.  Methyl Group-Induced Helicity in 1,4-Dimethylbenzo[c]phenanthrene and Its Metabolites: Synthesis, Physical, and Biological Properties , 2000 .

[53]  Yoshihisa Inoue,et al.  Chirality-sensing supramolecular systems. , 2008, Chemical reviews.

[54]  Joshua R. Smith,et al.  Synthesis and properties of molecular rods. 2. Zig-zag rods. , 2005, Chemical reviews.

[55]  S. Vyskocil,et al.  Synthesis of 3-hexahelicenol and its transformation to 3-hexahelicenylamines, diphenylphosphine, methyl carboxylate, and dimethylthiocarbamate. , 2003, The Journal of organic chemistry.

[56]  H. Nishide,et al.  Electro- and Magneto-Responsible Chiral Polymers , 2005 .

[57]  N. Branda,et al.  Chiral discrimination in hydrogen-bonded , 2000, Organic letters.

[58]  N. Harada,et al.  Light-driven monodirectional molecular rotor , 2022 .

[59]  André Persoons,et al.  Electric-field-modulated circular-difference effects in second-harmonic generation from a chiral liquid crystal. , 2002, Angewandte Chemie.

[60]  Ben L. Feringa,et al.  Dynamic Control and Amplification of Molecular Chirality by Circular Polarized Light , 1996, Science.

[61]  A. Persoons,et al.  Circular Dichroism and UV-Visible Absorption Spectra of the Langmuir-Blodgett Films of an Aggregating Helicene , 1998 .

[62]  C. Mcfadden,et al.  Adsorption of helical aromatic molecules: heptahelicene on Ni(1 1 1) , 2003 .

[63]  Hongming Yuan,et al.  Synthesis, structure, and photoelectronic effects of a uranium-zinc-organic coordination polymer containing infinite metal oxide sheets. , 2003, Journal of the American Chemical Society.

[64]  X. Meng,et al.  Dual modulation of a molecular switch with exceptional chiroptical properties. , 2005, Journal of the American Chemical Society.

[65]  F. Aloui,et al.  Synthesis and characterization of new hexahelicene derivatives , 2007 .

[66]  C. Nuckolls,et al.  Synthesis and Aggregation of a Conjugated Helical Molecule , 1999 .

[67]  Hiroki Sugiura,et al.  Synthesis and ring size effect of macrocyclic ethynylhelicene oligomers. , 2006, The Journal of organic chemistry.

[68]  H. Gottlieb,et al.  Diastereoisomeric charge-transfer complexes. Measurement of thermodynamic constants by 1H nuclear magnetic resonance spectroscopy , 1981 .

[69]  W. Dehaen,et al.  Expeditive syntheses of functionalized pentahelicenes and NC-AFM on Ag(001). , 2009, Organic letters.

[70]  Arnold L. Rheingold,et al.  Application of the Russig−Laatsch Reaction to Synthesize a Bis[5]helicene Chiral Pocket for Asymmetric Catalysis , 2000 .

[71]  Angela Marinetti,et al.  Synthesis and resolution of 2-(diphenylphosphino)heptahelicene , 2007 .

[72]  J. Chocholousová,et al.  An organometallic route to long helicenes , 2009, Proceedings of the National Academy of Sciences.

[73]  Vincenzo Balzani,et al.  Molecular Devices and Machines– A Journey into the Nano World , 2003 .

[74]  M. Yamaguchi,et al.  Synthesis of optically active macrocycles consisting of helical chiral unit 1,12-dimethylbenzo[c]phenanthrene-5,8-dicarboxylate as a novel chiral building block , 1996 .

[75]  J. Nishida,et al.  A Redox Switch Based on Dihydro[5]helicene: Drastic Chiroptical Response Induced by Reversible C-C Bond Making/Breaking upon Electron Transfer. , 2001, Angewandte Chemie.

[76]  V. Aggarwal,et al.  Catalytic asymmetric synthesis of epoxides mediated by chiral iminium salts , 1996 .

[77]  Matthew J. Mio,et al.  A field guide to foldamers. , 2001, Chemical reviews.

[78]  Y. Yokoyama,et al.  Chiral helicenoid diarylethene with large change in specific optical rotation by photochromism. , 2007, The Journal of organic chemistry.

[79]  R. Goddard,et al.  First enantioselective catalysis using a helical diphosphane , 1997 .

[80]  David A. Leigh,et al.  Dynamic Chirality: Molecular Shuttles and Motors , 2006 .

[81]  M. Yamaguchi,et al.  Synthesis of optically active bihelicenols , 2003 .

[82]  E. W. Meijer,et al.  Amplification of chirality in dynamic supramolecular aggregates. , 2007, Angewandte Chemie.

[83]  H. Higuchi,et al.  Electrochiroptical response of a hexaarylethane derivative with a helical π-skeleton: drastic UV–Vis and CD spectral changes upon electrolysis of 4′,5′-dibromodispiro[xanthene-9,9′(9′H,10′H)-phenanthrene-10′,9″-xanthene] , 2002 .

[84]  Chien-Tien Chen,et al.  Diastereoselective, synergistic dual-mode optical switch with integrated chirochromic helicene and photochromic bis-azobenzene moieties. , 2010, Organic letters.

[85]  B. K. Mandal,et al.  [5]helicene-fused phthalocyanine derivatives. New members of the phthalocyanine family. , 2003, The Journal of organic chemistry.

[86]  B. K. Mandal,et al.  New polyphenylated phthalocyanine derivatives , 2002 .

[87]  B. Feringa,et al.  In control of motion: from molecular switches to molecular motors. , 2001, Accounts of chemical research.

[88]  H. Higuchi,et al.  Electrochiroptical response of 2,2'-(2,2-diarylethenyl)binaphthyl-type electron donors that undergo reversible C-C bond formation/breaking upon two-electron transfer. , 2003, The Journal of organic chemistry.

[89]  Dominik Horinek,et al.  Artificial molecular rotors. , 2005, Chemical reviews.

[90]  R. Fasel,et al.  Orientation of chiral heptahelicene C30H18 on copper surfaces: An x-ray photoelectron diffraction study , 2001 .

[91]  C. Mcfadden,et al.  Nanostructured chiral surfaces , 1999 .

[92]  R. Nolte,et al.  Chiral architectures from macromolecular building blocks. , 2001, Chemical reviews.

[93]  Keisuke Suzuki,et al.  From Axial Chirality to Central Chiralities: Pinacol Cyclization of 2,2'-Biaryldicarbaldehyde to trans-9,10-Dihydrophenanthrene-9,10-diol. , 1999, Angewandte Chemie.

[94]  Hiroki Sugiura,et al.  [3+3]Cycloalkyne dimers linked by an azo group: a stable cis-azo compound forms polymeric aggregates by nonplanar pi-pi interactions. , 2003, Journal of the American Chemical Society.

[95]  R. Fasel,et al.  Coverage and Enantiomeric Excess Dependent Enantiomorphism in Two-Dimensional Molecular Crystals† , 2008 .

[96]  A. Yamagishi,et al.  STM observation of molecular chirality and alignment on solid surface , 2003 .

[97]  D. Lednicer,et al.  A NEW REAGENT FOR RESOLUTION BY COMPLEX FORMATION; THE RESOLUTION OF PHENANTHRO-[3,4-c]PHENANTHRENE1 , 1955 .

[98]  M. Yamaguchi,et al.  Macrocyclic Amides Consisting of Helical Chiral 1,12-Dimethylbenzo[c]phenanthrene-5,8-dicarboxylate , 1998 .

[99]  M. Yamaguchi,et al.  Two-component gel formation by pseudoenantiomeric ethynylhelicene oligomers. , 2010, Angewandte Chemie.

[100]  Kenso Soai,et al.  Asymmetric Induction by Helical Hydrocarbons: [6]‐ and [5]Helicenes , 2001 .

[101]  T. J. Katz,et al.  Asymmetric Synthesis of Helical Metallocenes , 1986 .

[102]  M. R. Imam,et al.  Dendron-mediated self-assembly, disassembly, and self-organization of complex systems. , 2009, Chemical reviews.

[103]  T. J. Katz,et al.  A [5]HELOL analogue that senses remote chirality in alcohols, phenols, amines, and carboxylic acids. , 2005, The Journal of organic chemistry.

[104]  H. Rau,et al.  Exciplex and ion pair quenching in a chiral hexahelicene-amine system , 1992 .

[105]  T. Bell,et al.  Supramolecular optical chemosensors for organic analytes. , 2004, Chemical Society reviews.

[106]  C. Nuckolls,et al.  Synthesis, Structure, and Properties of a Helical Columnar Liquid Crystal , 1998 .

[107]  S. Laschat,et al.  Discotic liquid crystals: from tailor-made synthesis to plastic electronics. , 2007, Angewandte Chemie.

[108]  A. Terfort,et al.  The First Helical-Chiral Phosphane Ligands: rac-[5]- and rac-[6]-Heliphos , 1997 .

[109]  Z. Wang,et al.  Long-distance chirality transfer in polymerization of isocyanides bearing a remote chiral group , 1997 .

[110]  D. Venkataraman,et al.  Probing the Chiroptical Response of a Single Molecule , 2006, Science.

[111]  R. Fasel,et al.  Amplification of chirality in two-dimensional enantiomorphous lattices , 2006, Nature.

[112]  A. Cohen,et al.  Limits on fluorescence detected circular dichroism of single helicene molecules. , 2009, The journal of physical chemistry. A.

[113]  M. Yamaguchi,et al.  Enantioselective hydrogenation of itaconate using rhodium bihelicenol phosphite complex. Matched/mismatched phenomena between helical and axial chirality , 2003 .

[114]  B. K. Mandal,et al.  First synthesis of 5(helicene) fused phthalocyanines: exceptional solubilities and long Q-band absorptions , 2002 .

[115]  Z. Wang,et al.  Synthesis and photochromic properties of helically locked 1,2-dithienylethenes , 1999 .

[116]  K. Ernst Expression and Amplification of Chirality in Two-Dimensional Molecular Crystals , 2008 .

[117]  Choongik Kim,et al.  Synthesis, characterization, and transistor response of tetrathia-[7]-helicene precursors and derivatives , 2009 .

[118]  R. H. Martin,et al.  Synthèses Asymétriques Potentielles Impliquant la Réaction “Ene” , 2010 .

[119]  T. Miyashita,et al.  Synthesis and monolayer behaviors of optically active 1,12- dimethylbenzo[c]phenanthrene-5,8-diamides and the formation of chiral langmuir-blodgett films , 1999 .

[120]  M. Yamaguchi,et al.  [3+3]Cycloalkyne oligomers: linking groups control intra- and intermolecular aggregation by pi-pi interactions. , 2003, Angewandte Chemie.

[121]  A. Persoons,et al.  Synthesis, Self-Assembly, and Nonlinear Optical Properties of Conjugated Helical Metal Phthalocyanine Derivatives , 1999 .

[122]  Masahiro Irie,et al.  Diarylethenes for Memories and Switches. , 2000, Chemical reviews.

[123]  T. J. Katz,et al.  Helical Discotic Liquid Crystals , 2003 .

[124]  A. Rheingold,et al.  Synthesis and properties of an optically active helical bis-cobaltocenium ion , 1993 .

[125]  Richard Martin,et al.  Diastereoselective NaBH4 Reductions of (dl) α‐Keto Esters , 2010 .

[126]  K. Ernst,et al.  Induction of homochirality in achiral enantiomorphous monolayers. , 2004, Journal of the American Chemical Society.

[127]  A. Yamagishi,et al.  Molecular chirality on a solid surface : thiaheterohelicene monolayer on gold imaged by STM , 2000 .

[128]  T. Bender,et al.  Synthesis of polyimides and segmented block copolyimides by transimidization , 2000 .

[129]  F. Diederich,et al.  Synthesis of the helicopodands: novel shapes for chiral clefts , 1991 .

[130]  D. Amabilino Chiral nanoscale systems: preparation, structure, properties and function. , 2009, Chemical Society reviews.

[131]  Béchir Ben Hassine,et al.  Synthèses Asymétriques et Synthèses Asymétriques Potentielles D'α-Amino Alcools: Hydroxyamination D'Oléfines par la Méthode de Sharpless , 2010 .

[132]  M. Yamaguchi,et al.  One-step synthesis of optically active cyclic polyamines containing helicene , 2002 .

[133]  M. Newman,et al.  The Synthesis and Resolution of 1,12-Dimethylbenzo[c]phenanthrene-5-acetic Acid1 , 1956 .

[134]  R. Fasel,et al.  Differences in two-dimensional crystal structures: Racemic and enantiopure heptahelicene on Cu(111) , 2004 .

[135]  M. Gingras,et al.  Synthesis of carbohelicenes and derivatives by “carbenoid couplings” , 1999 .

[136]  M. A. Shcherbina,et al.  Hollow six-stranded helical columns of a helicene. , 2009, Angewandte Chemie.

[137]  E. Yashima,et al.  Dynamic Helical Structures: Detection and Amplification of Chirality , 2007 .

[138]  H. Higuchi,et al.  Butane-1,4-diyl dications stabilized by steric factors: electrochiroptical response systems based on reversible interconversion between dihydro[5]helicene-type electron acceptors and electron-donating 1,1'-binaphthyls. , 2005, Organic & biomolecular chemistry.

[139]  M. Grunze,et al.  NEXAFS study on the orientation of chiral P-heptahelicene on Ni(100) , 2001 .

[140]  T. Aida,et al.  Toward intelligent molecular machines: directed motions of biological and artificial molecules and assemblies. , 2005, Chemical reviews.

[141]  D. Amabilino,et al.  Spontaneous resolution under supramolecular control. , 2002, Chemical Society reviews.

[142]  E. Yashima,et al.  Helical polymers: synthesis, structures, and functions. , 2009, Chemical reviews.

[143]  C. Rosini,et al.  Conformational and Configurational Analysis of 4,4‘-Biphenanthryl Derivatives and Related Helicenes by Circular Dichroism Spectroscopy and Cholesteric Induction in Nematic Mesophases , 1996 .

[144]  S. Sahasithiwat,et al.  3,12-Dimethoxy-7,8-dicyano-[5]helicene as a novel emissive material for organic light-emitting diode , 2010 .

[145]  T. Ross Kelly,et al.  Investigation of triptycene-based surface-mounted rotors , 2003 .

[146]  M. Albrecht,et al.  "Let's twist again"--double-stranded, triple-stranded, and circular helicates. , 2001, Chemical reviews.

[147]  Matthew T. Stone,et al.  A helicene-containing foldamer displaying highly solvent-dependent CD spectra. , 2004, Organic letters.

[148]  T. B. Norsten,et al.  Reversible [7]-thiahelicene formation using a 1,2-dithienylcyclopentene photochrome. , 2001, Journal of the American Chemical Society.

[149]  S. Denmark,et al.  Catalytic asymmetric synthesis. , 2000, Accounts of chemical research.

[150]  Junji Mizukami,et al.  Synthesis of Helicenediamine Oligomers and Their Formation of Multilayer Structures in Aqueous Solvents , 2006 .

[151]  O. Melnyk,et al.  Reaction of Isocyanate-Functionalised Silicon Wafers with Complex Amino Compounds , 2007 .

[152]  M. Ward,et al.  Synthesis and Properties of Optically Active Helical Metallocene Oligomers , 1993 .

[153]  Masao Nakazaki,et al.  Synthesis and chiral recognition of novel crown ethers incorporating helicene chiral centres , 1983 .

[154]  M. Yamaguchi,et al.  Hetero-double-helix formation by an ethynylhelicene oligomer possessing perfluorooctyl side chains. , 2008, The Journal of organic chemistry.

[155]  D. Šaman,et al.  A Convenient Route to 2‐Hydroxy‐ and 2,15‐Dihydroxyhexahelicene , 2007 .

[156]  Colin Nuckolls,et al.  Second-order nonlinear optical properties of highly symmetric chiral thin films , 2001 .

[157]  Hiroko Nakagawa,et al.  Study of chiral recognition of bilayered phosphatidylcholine vesicles using a helicene probe: characteristic function of cholesterol. , 2003, Chirality.

[158]  T. R. Kelly,et al.  Progress toward a rationally designed, chemically powered rotary molecular motor. , 2007, Journal of the American Chemical Society.

[159]  T. Bender,et al.  Polyimide thin films produced by direct solid-state polymerization of an amino anhydride monomer , 2000 .

[160]  M. Yamaguchi,et al.  Chiral recognition in noncovalent bonding interactions between helicenes: right-handed helix favors right-handed helix over left-handed helix. , 2008, Organic & biomolecular chemistry.

[161]  L. Pu,et al.  The First Dendrimer‐Based Enantioselective Fluorescent Sensor for the Recognition of Chiral Amino Alcohols , 2000 .

[162]  J. W. Cook 378. Polycyclic aromatic hydrocarbons. Part XII. The orientation of derivatives of 1 : 2-benzanthracene, with notes on the preparation of some new homologues, and on the isolation of 3 : 4 : 5 : 6-dibenzphenanthrene , 1933 .

[163]  R. Raval,et al.  Extended surface chirality from supramolecular assemblies of adsorbed chiral molecules , 2000, Nature.

[164]  Manfred T. Reetz,et al.  Kinetic resolution in Pd-catalyzed allylic substitution using the helical PHelix ligand , 2000 .

[165]  K. Ernst Amplification of chirality in two-dimensional molecular lattices , 2008 .

[166]  F. Diederich,et al.  Geometrical optimisation of 1,1′-binaphthalene receptors for enantioselective molecular recognition of excitatory amino acid derivatives , 1998 .

[167]  R. Fasel,et al.  Chirality transfer from single molecules into self-assembled monolayers. , 2003, Angewandte Chemie.

[168]  Markus Albrecht,et al.  Artificial molecular double-stranded helices. , 2005, Angewandte Chemie.

[169]  Alan E. Rowan,et al.  Helical Molecular Programming , 1998 .

[170]  T R Kelly,et al.  Progress toward a rationally designed molecular motor. , 2001, Accounts of chemical research.

[171]  Kenso Soai,et al.  Enantioselective synthesis induced by tetrathia-[7]-helicenes in conjunction with asymmetric autocatalysis , 2006 .

[172]  N. Clark,et al.  ELECTRO-OPTIC SWITCHING BY HELICENE LIQUID CRYSTALS , 2002 .

[173]  C. Nuckolls,et al.  Aggregation of Conjugated Helical Molecules , 1996 .

[174]  Katz,et al.  Why (1S)-Camphanates Are Excellent Resolving Agents for Helicen-1-ols and Why They Can Be Used to Analyze Absolute Configurations. , 2000, The Journal of organic chemistry.

[175]  M. Yamaguchi,et al.  Synthesis and structure of built-up organic macromolecules containing helicene. , 2008, Chemical record.

[176]  T. Bender,et al.  Poly(aryl ether)s containing o-terphenyl subunits. III. Random copoly(ether imide)s , 2000 .

[177]  T. Miyashita,et al.  Spreading Behavior of Optically Active Macrocycloamides Consisting of Helical Chiral Units at the Air−Water Interface and the Formation of Langmuir−Blodgett Films , 1998 .

[178]  F. Diederich,et al.  A New Helicopodand: Molecular Recognition of Dicarboxylic Acids with High Diastereoselectivity , 1993 .

[179]  M. P. Neal,et al.  Helical twisting power and chirality indices , 2004 .

[180]  Koji Yamamoto,et al.  Mechanically directed absolute asymmetric syntheses of helicenes in a twisted nematic mesophase , 1979 .

[181]  B. K. Mandal,et al.  Self-assembled, nano-structured octaalkoxy helicenocyanines , 2006 .

[182]  M. Gingras,et al.  Syntheses of [5]-helicene by McMurry or carbenoid couplings , 1998 .

[183]  T. R. Kelly,et al.  Troubleshooting a molecular motor: a remarkably stable N-acyl pyridinium salt , 2008 .

[184]  R. Raval Chiral expressions at metal surfaces , 2003 .

[185]  Tetsuo Ikeda,et al.  Synthesis and chiral recognition of optically active crown ethers incorporating a helicene moiety as the chiral centre , 1990 .

[186]  M. Yamaguchi,et al.  Recognition of Helicity by Native Cyclodextrins.Highly Enantioselective Complexation of Tetrahelicene Dicarboxylic Acid with β-Cyclodextrin , 1998 .

[187]  M. Rohlfing,et al.  Toward Molecular Nanowires Self-Assembled on an Insulating Substrate: Heptahelicene-2-carboxylic acid on Calcite (1014) , 2010 .

[188]  J. N. Moorthy,et al.  Facile synthesis, fluorescence, and photochromism of novel helical pyrones and chromenes. , 2006, Organic letters.

[189]  K. Nakamura,et al.  Synthesis and self-aggregation of cyclic alkynes containing helicene. , 2001, Organic letters.

[190]  M. Yamaguchi,et al.  Chiral recognition in the binding of helicenediamine to double strand DNA: interactions between low molecular weight helical compounds and a helical polymer. , 2002, Bioorganic & medicinal chemistry.

[191]  Francesco Zerbetto,et al.  Synthetic molecular motors and mechanical machines. , 2007, Angewandte Chemie.

[192]  Manfred T. Reetz,et al.  2,15-Dihydroxy-hexahelicene (HELIXOL): synthesis and use as an enantioselective fluorescent sensor , 2001 .

[193]  T. J. Katz,et al.  Synthesis of a Helical Conjugated Ladder Polymer , 1996 .

[194]  P. Sidebottom,et al.  Structural specificity in asymmetric charge-transfer complexation of helicenes , 1982 .

[195]  W. H. Laarhoven,et al.  The influence of the chiral environment in the photosynthesis of enantiomerically enriched hexahelicene. A sudden change in the chirality of hexahelicene by a change in the temperature of a chiral crystalline medium. , 1995 .

[196]  B. Feringa,et al.  A Highly Stereoselective Optical Switching Process Based on Donor–Acceptor Substituted Dissymmetric Alkenes , 1995 .

[197]  D. Venkataraman,et al.  Dissymmetries in fluorescence excitation and emission from single chiral molecules. , 2009, Chirality.

[198]  M. Yamaguchi,et al.  Folding of dihelicenetriamines in water , 2002 .

[199]  M. R. Imam,et al.  Molecular structure of helical supramolecular dendrimers. , 2008, Journal of the American Chemical Society.

[200]  T. Bender,et al.  Soluble alternating copolyimides containing the tetrahydro[5]helicene unit , 1998 .

[201]  T. Bender,et al.  Condensation polyimides from AB-type amino anhydride monomers , 1997 .

[202]  Masood Parvez,et al.  7:8,9:10-dibenzo-1,2,3,4-tetrafluoro- triphenylene: synthesis, structure, and photophysical properties of a novel [5]helicene. , 2005, The Journal of organic chemistry.

[203]  Spencer D. Dreher,et al.  [5]HELOL Phosphite: A Helically Grooved Sensor of Remote Chirality , 2000 .

[204]  Ricardo Martin,et al.  Utilisation de la Synthèse Atrolactique Pour L'Évaluation de L'Efficacité D'Inducteurs de Synthèse Asymétrique , 2010 .