Chiral nanotechnology

Chirality

Volumn 17, Issue 7, 2005, Pages 404-420

  Zhang, Jing ^a   Albelda, M Teresa ^a   Liu, Yu ^a   Canary, James W ^a  

^a NEW YORK UNIVERSITY   (United States)

Author keywords

Asymmetric synthesis; Chiral fullerenes; Chiral nanotechnology; Chiral nanotubes; Chiral separations; Chiral supramolecules; DNA nanotechnology; Enantiomeric analysis; Molecular devices

Indexed keywords

FULLERENE DERIVATIVE; NANOTUBE;

ASYMMETRIC SYNTHESIS; CHIRALITY; ENANTIOMER; NANOTECHNOLOGY; PRIORITY JOURNAL; REVIEW; SUPRAMOLECULAR CHEMISTRY;

EID: 22844441238     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20178     Document Type: Review

References (99)

1. Paull R, Wolfe J, Hebert P, Sinkula M. Investing in nanotechnology. Nat Biotechnol 2003;21:1144-1147.
2. Roco M. Nanotechnology: convergence with modern biology and medicine. Curr Opin Biotechnol 2003;14:337-346.
3. Balzani V, Venturi M, Credi A. Molecular devices and machines-a journey into the nanoworld. Weinheim, Germany: Wiley-VCH; 2003. p 2-4.
4. Green MM, Nolle RJM, Meijer EW, Denmark SE, Siegel J. Topics in stereochemistry. Vol 24. Materials-chirality. New York: Wiley-VCH; 2003.
5. Dieguez M, Pamies O, Claver C. Ligands derived from carbohydrates for asymmetric catalysis. Chem Rev 2004;104:3189-3215.
6. Hawkins JM, Watson TJN. Asymmetric catalysis in the pharmaceutical industry. Angew Chem Int Ed 2004;43:3224-3228.
7. Ngo HL, Hu A, Lin W. Molecular building block approaches to chiral porous zirconium phosphonates for asymmetric catalysis. J Mol Catal A: Chem 2004;215:177-186.
8. Hu A, Ngo HL, Lin W. Chiral porous hybrid solids for practical heterogeneous asymmetric hydrogenation of aromatic ketones. J Am Chem Soc 2003;125:11490-11491.
9. Hu A, Ngo HL, Lin W. Chiral, porous, hybrid solids for highly enantioselective heterogeneous asymmetric hydrogenation of β-keto esters. Angew Chem Int Ed 2003;42:6000-6003.
10. Sivaguru J, Poon T, Franz R, Jockusch S, Adam W, Turro NJ. Stereocontrol within confined spaces: enantioselective photooxidation of enecarbamates inside zeolite supercages. J Am Chem Soc 2004; 126:10816-10817.
11. Poon T, Turro NJ, Chapman J, Lakshminarasimhan P, Lei X, Adam W, Bosio SG. A supramolecular "ship in bottle" strategy for enantiomeric selectivity in geminate radical pair recombination. Org Lett 2003;5: 2025-2028.
12. Wong W-L, Huang K-H, Teng P-F, Lee C-S, Kwong H-L. A novel chiral terpyridine macrocycle as a fluorescence sensor for enantioselective recognition of amine acid derivatives. Chem Commun 2004:384-385.
13. Yashima E, Maeda K, Nishimura T. Detection and amplification of chirality by helical polymers. Chem Eur J 2004;10:42-51.
14. Dutta P, Tipple CA, Lavrik NV, Datskos PG, Hofstetter H, Hofsletter O, Sepaniak MJ. Enantioselective sensors based on antibody-mediated nanomechanics. Anal Chem 2003;75:2342-2348.
15. Kawamura A, Hindi S. Protein fishing with chiral molecular baits. Chirality 2005;17(6):332-337.
16. Prince RB, Barnes SA, Moore JS. Foldamer-based molecular recognition. J Am Chem Soc 2000;122:2758-2762.
17. Borovkov W, Hembury GA, Inoue Y. Origin, control, and application of supramolecular chirogenesis in bisporphyrin-based systems. Acc Chem Soc 2004;37:449-459.
18. Huang X, Nakanishi K, Berova N. Porphyrins and metalloporphyrins: versatile circular dichroic reporter groups for structural studies. Chirality 2000;12:237-255.
19. Allenmark S. Induced circular dichroism by chiral molecular interaction. Chirality 2003;15:409-422.
20. Higuchi A, Higuchi Y, Furuta K, Yoon BO, Hara M, Maniwa S, Saitoh M, Sanui K. Chiral separation of phenylalanine by ultrafiltration through immobilized DNA membranes. J Mater Sci 2003; 221:207-208.
21. Lee SB, Mitchell DT, Trofin L, Nevanen TK, Soderlind H, Martin CR. Antibody-based bio-nanotube membranes for enantiomeric drug separations. Science 2002;296:2198-2200.
22. Fireman-Shoresh S, Avnir D, Marx S. General method for chiral imprinting of sol-gel thin films exhibiting enantioselectivity. Chem Mater 2003;15:3607-3613.
23. 2 films associated with field-effect transistors: novel functionalized devices for chirospecific analyses. Chem Eur J 2001;7:3992-3997.
24. Palmer CP, McCarney JP. Development in the use of soluble ionic polymers as pseudo-stationary phases for electrokinetic chromatography and stationary phases for electrochromatography. J Chromatogr A 2004;1044(1-2):159-176.
25. Becker JJ, Gagne MR. Imprinting chiral information into rigidified dendrimers. Organometallics 2003;22:4984-4998.
26. Feringa BL. Molecular switches. Weinheim, German: Wiley-VCH; 2001.
27. Feringa BL, van Delden RA, Koumura N, Geertsema E. Chiroptical molecular switches. Chem Rev 2000;100:1789-1816.
28. Zahn S, Canary JW. Electron-induced inversion of helical chirality in copper complexes of N,N-dialkylmethionines. Science 2000;288: 1404-1407.
29. Barcena HS, Holmes AE, Zahn S, Canary JW. Redox inversion of helicity in propeller-shaped molecules derived from S-methyl cysteine and methioninol. Org Lett 2003;5:709-711.
30. Zahn S, Canary JW. Cu(I/II) redox control of molecular conformation and shape in chiral tripodal ligands: binary exciton-coupled circular dichroic states. J Am Chem Soc 2002;124:9204-9211.
31. Zahn S, Canary JW. Redox-switched exciton-coupled circular dichroism: A novel strategy for binary molecular switching. Angew Chem Int Ed 1998;37:305-307.
32. Cheon KS, Selinger JV, Green MM. Counterintuitive influence of microscopic chirality on helical order in polymers. J Phys Org Chem 2004;17:719-723.
33. Fujiki M, Koe JR, Terao K, Sato T, Teramoto A, Watanabe J. Optically active polysilanes. Ten years of progress and new polymer twist for nanoscience and nanotechnology. Polym J 2003;35:297-344.
34. Tabei J, Nomura R, Sanda F, Masuda T. Design of helical poly(N-propargylamides) that switch the helix sense with thermal stimuli. Macromolecules 2004;37:1175-1179.
35. Kim SY, Fujiki M, Ohira A, Kwak G, Kawakami Y. Thermodriven chiroptical switching of a polysilane thin film. Macromolecules 2004; 37:4321-4324.
36. Davis AP. Synthetic molecular motors. Nature 1999;401:120-121.
37. Feringa BL. In control of motion: from molecular switches to molecular motors. Acc Chem Res 2001;34:504-513.
38. van Delden RA, ter Wiel MKJ, Feringa BL. A chiroptical molecular switch with perfect stereocontrol. Chem Commun 2004;200-201.
39. Koumura N, Zijistra RWJ, van Delden RA, Harada N, Feringa BL. Light-driven monodirectional molecular rotor. Nature 1999;401: 152-155.
40. Koumura N, Geertsema EM, Meetsma A, Feringa BL. Light-driven molecular rotor: unidirectional rotation controlled by a single stereogenic center. J Am Chem Soc 2000;122:12005-12006.
41. Koumura N, Geertsema EM, van Gelder MB, Meetsma A, Feringa BL. Second generation light-driven molecular motors. Unidirectional rotation controlled by a single stereogenic center with near-perfect photoequilibria and acceleration of the speed of rotation by structural modification. J Am Chem Soc 2002;124: 5037-5051.
42. ter Wiel MKJ, van Delden RA, Meetsma A, Feringa BL. Increased speed of rotation for the smallest light-driven molecular motor. J Am Chem Soc 2003;125:15076-15086.
43. Kelly TR, de Silva H, Silva RA. Unidirectional rotary motion in a molecular system. Nature 1999;401:150-152.
44. Kelly TR, Silva RA, de Silva H, Jasmin S, Zhao Y. A rationally designed prototype of a molecular motor. J Am Chem Soc 2002;122:6935-6949.
45. Kelly TR. Progress toward a rationally designed molecular motor. Acc Chem Res 2001;34:514-522.
46. Cornelissen JJLM, Rowan AE, Nolle RJM, Sommerdijk NAJM. Chiral architectures from macromolecular building blocks. Chem Rev 2001; 101:4039-4070.
47. Kozlovsky MV. Chiral polymers with photoaffected phase behaviour for photo-optical and optoelectronic applications. Synth Met 2002; 127:67-70.
48. Lin SH, Hsu KY, Chen WZ, Whang WT. Phenanthrenequinone-doped poly(methyl methacrylate) photopolymer bulk for volume holographic data storage. Opt Lett 2000;25:451-453.
49. Liu JH, Yang PC. Preparation and optical performance of chiral polymers having azobenzene segments. J Appl Polym Sci 2004;91: 3693-3704.
50. Whitesides GM, Grzybowski B. Self-assembly at all scales. Science 2002;295:2418-2421.
51. Mateos-Timoneda MA, Crego-Calama M, Reinhoudt DN. Supramolecular chirality of self-assembled systems in solution. Chem Soc Rev 2004;33:363-372.
52. Prins IJ, de Jong F, Timmerman P, Reinhoudt DN. An enantiomerically pure hydrogen-bonded assembly. Nature 2000;408:181-184.
53. Prins LJ, Verhage JJ, de Jong F, Timmerman P, Reinhoudt DN. Enantioselective noncovalent synthesis of hydrogen-bonded double-rosette assemblies. Chem Eur J 2002;8:2302-2313.
54. Ishi-I T, Crego-Calama M, Timmerman P, Reinhoudt DN, Shinkai S. Self-assembled receptors for enantioselective recognition of chiral carboxylic acids in a highly cooperative manner. Angew Chem Int Ed 2002;41:1924-1929.
55. van Gorp JJ, Vekemans JAJM, Meijer EW. Cs-Symmetrical supramolecular architectures: fibers and organic gels from discotic trisamides and trisureas. J Am Chem Soc 2002;124:14759-14769.
56. Brunsveld L, Vekemans JAJM, Hirschberg JHKK, Sijbesma RP, Meijer EW. Hierarchical formation of helical supramolecular polymers via stacking of hydrogen-bonded pairs in water. Proc Natl Acad Sci USA 2002;99:4977-4982.
57. Percec V, Dulcey AE, Balagurusamy VSK, Miura Y, Smidrkal J, Peterca M, Nummelin S, Edlund U, Hudson SD, Heiney PA, Duan H, Magonov SN, Vinogradov SA. Self-assembly of amphiphilic dendritic dipeptides into helical pores. Nature 2004;430:764-768.
58. Slager J, Cohen Y, Khalfin R, Talmon Y, Domb AJ. Peptides form stereoselective complexes with chiral polymers. Macromolecules 2003;36:2999-3000.
59. Fenniri H, Deng BL, Ribbe AE. Helical rosette nanotubes with tunable chiroptical properties. J Am Chem Soc 2002;124:11064-11072.
60. Cui Y, Lee SJ, Lin W. Interlocked chiral nanotubes assembled from quintuple helices. J Am Chem Soc 2003;125:6014-6015.
61. Ghadiri MR, Granja JR, Buehler LK. Artificial transmembrane ion channels from self-assembling pepticle nanotubes. Nature 1994;369: 301-304.
62. Hartgerink JD, Clark TD, Ghadiri MR. Peptide nanotubes and beyond. Chem Eur J 1998;4(8):1367-1372.
63. Bong DT, Clark TD, Granja JR, Ghadiri MR. Self-assembling organic nanotubes. Angew Chem Int Ed 2001;40:988-1011.
64. Martin CR, Kohli P. The emerging field of nanotube biotechnology. Nature 2003;2:29-37.
65. Fernandez-Lopez S, Kim HS, Choi EC, Delgado M, Granja JR, Khasanov A, Kraehenbuehl K, Long G, Weinberger DA, Wilcoxen KM, Ghadiri MR. Antibacterial agents based on the cyclic D,L-α-peptide architecture. Nature 2001;412:452-455.
66. Sakai N, Matile S. Programmed assembly of rigid-rod β-barrel pores: thermal inversion of chirality. Chirality 2004;16:S28-S35.
67. Severin K, Lee DH, Kennan AJ, Ghadiri MR. A synthetic pepticle ligase. Nature 1997;389:706-709.
68. Saghatelian A, Yokobayashi Y, Soltani K, Ghadiri MR. A chiroselective peptide replicator. Nature 2001;409:797-801.
69. Mitchell DT, Lee SB, Trofin L, Li N, Nevanen TK, Söderlund H, Martin CR. Smart nanotubes for bioseparations and biocatalysis. J Am Chem Soc 2002;124:11864-11865.
70. Terrones M, Terrones G, Terrones H. Structure, chirality and formation of giant icosahedral fullerenes and spherical graphitic onions. Struct Chem 2002;13:373-384.
71. Terrones H, Terrones M. Curved nanostructured materials. New J Phys 2003;5:126.
72. Fanti M, Orlando G, Poggi G, Zerbetto F. Semiempirical quantum-chemical assignment of the circular dichroism spectra of small chiral fullerenes. Chem Phys 1997;223:159-168.
73. Ishi-i T, Shinkai S. Synthesis of chiral [60]fullerene-steroid bisadducts using steroid templates. Tetrahedron 1999;55:12515-12530.
74. Langer JJ, Golczak S, Gibinski T. Nitrofullerene CT complexes. A new family of chiral fullerene derivatives. Synth Met 2001;120:715-716.
75. Mamane V, Riant O. Asymmetric synthesis of chiral ferrocenyl fulleropyrrolidines as potential building blocks for new materials. Tetrahedron 2001;57:2555-2561.
76. Campidelli S, Eng C, Saez I, Goodby JW, Deschenaux R. Functional polypedes-chiral nematic fullerenes. Chem Commun 2003; 1520-1521.
77. Nishimura T, Takatani K, Sakurai S, Maeda K, Yashima E. A helical array of pendant fullerenes on an optically active polyphenylacetylene. Angew Chem 2002;114:3754-3756.
78. 2-symmetric chiral [60]fullerene-bisadducts. J Am Chem Soc 2004;126:11711-11717.
79. Ball P. Roll up for the revolution. Nature 2001;414:142-144.
80. Maiti A. Bandgap engineering with strain. Nature 2003;2:440-442.
81. Odom TW, Huang JL, Kim P, Lieber CM. Atomic structure and electronic properties of single-walled carbon nanotubes. Nature 1998;391:62-64.
82. Wildöer JWG, Venema LC, Rinzler AG, Smalley RE, Dekker C. Electronic structure of atomically resolved carbon nanotubes. Nature 1998;391:59-62.
83. Ivchenko EL, Spivak B. Chirality effects in carbon nanotubes. Phys Rev B: Condens Matter 2002;66(15):155404-1-155404-9.
84. Baughman RH, Zakhidov AA, de Heer WA. Carbon nanotubes-the route toward applications. Science 2002;297:787-792.
85. Wang A, Humphreys ES, Cheng SY, Delduco DF, Lustig SR, Wang H, Parker KN, Rizzo NW, Subramoney S, Chiang YM, Jagota A. Peptides with selective affinity for carbon nanotubes. Nature 2003;2:196-200.
86. Holzinger M, Vostrowsky O, Hirsch A, Hennrich F, Kappes M, Weiss R, Jellen F. Sidewall functionalization of carbon nanotubes. Angew Chem Int Ed 2001;40(21):4002-4005.
87. Yang Y, Wan M. Chiral nanotubes of polyaniline synthesized by a template-free method. J Mater Chem 2002;12:897-901.
88. Ito Y, Fukusaki E. DNA as a "nanomaterial". J Mol Catal B: Enzym 2004;28:155-166.
89. Du SM, Seeman NC. Synthesis of a DNA knot containing both positive and negative nodes. J Am Chem Soc 1992;114:9652-9655.
90. Du SM, Stollar BD, Seeman NC. A synthesis DNA molecule in three knotted topologies. J Am Chem Soc 1995;117:1194-1200.
91. Flapan E. Topological rubber gloves. J Math Chem 1998;23:31-49.
92. Bucka A, Stasiak A. Construction and electrophoretic migration of single-stranded DNA knots and catenanes. Nucleic Acids Res 2002;30(6):e24/1-e24/ 6.
93. Seeman NC, Lukeman PS. Nucleic acid nanostructures: bottom-up control of geometry on the nanoscale. Rep Prog Phys 2005;68:237-270.
94. Mitchell JC, Harris R, Malo J, Bath J, Turberfield AJ. Self-assembly of chiral DNA nanotubes. J Am Chem Soc 2004;126: 16342-16343.
95. Fu TJ, Seeman NC. DNA double-crossover molecules. Biochem 1993;32:3211-3220.
96. Niemeyer CM, Adler M. Nanomechanical devices based on DNA. Angew Chem Int Ed 2002;41:3779-3783.
97. Mao C, Sun W, Seeman NC. A DNA nanomechanical device based on the B-Z transition. Nature 1999;397:144-146.
98. Yan H, Zhang X, Shen Z, Seeman NC. A robust DNA mechanical device controlled by hybridization topology. Nature 2002;415: 62-65.
99. Tian Y, Mao C. Molecular gears: A pair of DNA circles continuously rolls against each other. J Am Chem Soc 2004;126:11410-11411.