Chiroptical switches: Applications in sensing and catalysis

Molecules

Volumn 17, Issue 2, 2012, Pages 1247-1277

  Dai, Zhaohua ^a   Lee, Jennifer ^b   Zhang, Wenyao ^a  

^a PACE UNIVERSITY   (United States)

^b NEW YORK UNIVERSITY   (United States)

Author keywords

Achiral analyte; Asymmetric catalysis; Chiral analyte; Chiroptical switches; Molecular recognition; Sensor

Indexed keywords

CATALYSIS; CIRCULAR DICHROISM; LIMIT OF DETECTION; OPTICS; REVIEW; ULTRAVIOLET SPECTROPHOTOMETRY;

CATALYSIS; CIRCULAR DICHROISM; LIMIT OF DETECTION; OPTICS AND PHOTONICS; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 84863180944     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17021247     Document Type: Review

References (98)

1. Castagnetto, J.M.; Xu, X.; Berova, N.; Canary, J.W. Absolute configurational assignment of self-organizing asymmetric tripodal ligand-metal complexes. Chirality1997, 9, 616-622.
2. Chiu, Y.-H.; dos Santos, O.; Canary, J.W. Conformational control of propeller-like chirality in Zn(II) complexes: Tightly balanced steric bias. Tetrahedron 1999, 55, 12069-12078. (Pubitemid 29453677)
3. Stoll, R.S.; Hecht, S. Artificial light-gated catalyst systems. Angew. Chem. Int. Ed. 2010, 49, 5054-5075.
4. Bartók, M. Unexpected inversions in asymmetric reactions: Reactions with chiral metal complexes, chiral organocatalysts, and heterogeneous chiral catalysts. Chem. Rev. 2009, 110, 1663-1705.
5. Feringa, B.L. Molecular Switches; Wiley-VCH: Weinheim, Germany, 2001.
6. Feringa, B.L. The art of building small: From molecular switches to molecular motors. J. Org. Chem. 2007, 72, 6635-6652. (Pubitemid 47434879)
7. Saha, S.; Stoddart, J.F. Photo-driven molecular devices. Chem. Soc. Rev. 2007, 36, 77-92. (Pubitemid 44973734)
8. Nakano, T.; Okamoto, Y. Synthetic helical polymers: Conformation and function. Chem. Rev. 2001, 101, 4013-4038. (Pubitemid 35373051)
9. Yashima, E.; Maeda, K.; Iida, H.; Furusho, Y.; Nagai, K. Helical polymers: Synthesis, structures, and functions. Chem. Rev. 2009, 109, 6102-6211.
10. Canary, J.W. Redox-triggered chiroptical molecular switches. Chem. Soc. Rev. 2009, 38, 747-756.
11. Canary, J.W.; Mortezaei, S.; Liang, J. Transition metal-based chiroptical switches for nanoscale electronics and sensors. Coord. Chem. Rev. 2010, 254, 2249-2266.
12. Canary, J.W.; Mortezaei, S.; Liang, J. Redox-reconfigurable tripodal coordination complexes: Stereodynamic molecular switches. Chem. Commun. 2010, 46, 5850-5860.
13. Canary, J.W.; Dai, Z. Dynamic stereochemistry and chiroptical spectroscopy of metallo-organic compounds. In Comprehensive Chiroptical Spectroscopy, Berova, N., Woody, R.W., Polavarapu, P., Nakanishi, K., Eds.; John Wiley & Sons: Hoboken, NJ, USA, 2012; Volume 2.
14. Canary, J.W.; Dai, Z.; Mortezaei, S. Spectroscopic analysis: Chiroptical sensors. In Comprehensive Chirality, Tranter, G., Ed.; Elsevier: Oxford, UK, 2012.
15. Miyake, H.; Tsukube, H. Helix architecture and helicity switching via dynamic metal coordination chemistry. Supramol. Chem. 2005, 17, 53-59.
16. Nakanishi, K.; Berova, N.; Woody, R. Circular Dichroism: Principles and Applications; Wiley-VCH: New York, NY, USA, 2000.
17. Yoneda, H.; Nakashima, Y.; Sakaguchi, U. Laser photochemistry. I. Partial photoresolution of tris(acetylacetonato)chromium(III) and related complexes. Chem. Lett. 1973, 1343-1346.
18. Urry, D.W.; Eyrin, H. Optical rotatory dispersion studies of L-histidine chelation. J. Am. Chem. Soc. 1964, 86, 4574-4580.
19. Taniguchi, T.; Monde, K.; Nishimura, S.-I.; Yoshida, J.; Sato, H.; Yamagishi, A. Rewinding of helical systems by use of the Cr(III) complex as a photoresponsive chiral dopant. Mol. Cryst. Liq. Cryst. 2006, 460, 107-116. (Pubitemid 44956332)
20. Montgomery, C.P.; New, E.J.; Parker, D.; Peacock, R.D. Enantioselective regulation of a metal complex in reversible binding to serum albumin: Dynamic helicity inversion signalled by circularly polarised luminescence. Chem. Commun. 2008, 4261-4263.
21. Hembury, G.A.; Borovkov, V.V.; Inoue, Y. Chirality-sensing supramolecular systems. Chem. Rev. 2008, 108, 1-73. (Pubitemid 351176405)
22. Canary, J.W.; Holmes, A.E.; Liu, J. Prospects for circular dichroism detection of nonracemic extraterrestrial organic molecules. Enantiomer 2001, 6, 181-188. (Pubitemid 32910192)
23. Joyce, L.A.; Maynor, M.S.; Dragna, J.M.; da Cruz, G.M.; Lynch, V.M.; Canary, J.W.; Anslyn, E.V. A simple method for the determination of enantiomeric excess and identity of chiral carboxylic acids. J. Am. Chem. Soc. 2011, 133, 13746-13752.
24. Nieto, S.; Lynch, V.M.; Anslyn, E.V.; Kim, H.; Chin, J. Rapid enantiomeric excess and concentration determination using simple racemic metal complexes. Org. Lett. 2008, 10, 5167-5170.
25. Nieto, S.; Lynch, V.M.; Anslyn, E.V.; Kim, H.; Chin, J. High-throughput screening of identity, enantiomeric excess, and concentration using MLCT transitions in CD spectroscopy. J. Am. Chem. Soc. 2008, 130, 9232-9233. (Pubitemid 352031124)
26. Zhang, J. Redox Triggered Molecular Mechanics. Ph.D. Dissertation, New York University, New York, NY, USA, 2005.
27. Dai, Z.; Xu, X.; Canary, J.W. Rigidified tripodal chiral ligands in the asymmetric recognition of amino compounds. Chirality 2005, 17, S227-S233. (Pubitemid 40962083)
28. Berova, N.; Pescitelli, G.; Petrovic, A.G.; Proni, G. Probing molecular chirality by CD-sensitive dimeric metalloporphyrin hosts. Chem. Commun. 2009, 5958-5980.
29. Li, X.; Borhan, B. Prompt determination of absolute configuration for epoxy alcohols via exciton chirality protocol. J. Am. Chem. Soc. 2008, 130, 16126-16127.
30. Borovkov, V.V.; Lintuluoto, J.M.; Inoue, Y. Supramolecular chirogenesis in bis(zincporphyrin): An absolute configuration probe highly sensitive to guest structure. Org. Lett. 2000, 2, 1565-1568.
31. Borovkov, V.V.; Hembury, G.A.; Inoue, Y. Origin, control, and application of supramolecular chirogenesis in bisporphyrin-based systems. Acc. Chem. Res. 2004, 37, 449-459.
32. Anderson, M.; Wilcox, K.; Guericke, M.; Chu, H.; Wilson, M.; Wilson, E.; Lucas, K.; Holmes, A.E. Enantio-discrimination of methamphetamine by circular dichroism using porphyrin tweezers. Chirality 2010, 22, 398-402.
33. Ishii, H.; Chen, Y.; Miller, R.A.; Karady, S.; Nakanishi, K.; Berova, N. Chiral recognition of cyclic alpha-hydroxyketones by CD-sensitive zinc tetraphenylporphyrin tweezer. Chirality 2005, 17, 305-315. (Pubitemid 40962091)
34. Guo, Y.M.; Oike, H.; Aida, T. Chiroptical transcription of helical information through supramolecular harmonization with dynamic helices. J. Am. Chem. Soc. 2004, 126, 716-717. (Pubitemid 38114346)
35. Li, W.S.; Jiang, D.L.; Suna, Y.; Aida, T. Cooperativity in chiroptical sensing with dendritic zinc porphyrins. J. Am. Chem. Soc. 2005, 127, 7700-7702. (Pubitemid 40745958)
36. Aimi, J.; Oya, K.; Tsuda, A.; Aida, T. Chiroptical sensing of asymmetric hydrocarbons using a homochiral supramolecular box from a bismetalloporphyrin rotamer. Angew. Chem. Int. Ed. 2007, 46, 2031-2035. (Pubitemid 46973662)
37. Choi, J.K.; Sargsyan, G.; Shabbir-Hussain, M.; Holmes, A.E.; Balaz, M. Chiroptical detection of condensed nickel(II)-Z-DNA in the presence of the B-DNA via porphyrin exciton coupled circular dichroism. J. Phys. Chem. B 2011, 115, 10182-10188.
38. Iwaniuk, D.P.; Wolf, C. A stereodynamic probe providing a chiroptical response to substratecontrolled induction of an axially chiral arylacetylene framework. J. Am. Chem. Soc. 2011, 133, 2414-2417.
39. Katoono, R.; Kawai, H.; Fujiwara, K.; Suzuki, T. Dynamic Molecular propeller: Supramolecular chirality sensing by enhanced chiroptical response through the transmission of point chirality to mobile helicity. J. Am. Chem. Soc. 2009, 131, 16896-16904.
40. Fenniri, H.; Deng, B.-L.; Ribbe, A.E. Helical rosette nanotubes with tunable chiroptical properties. J. Am. Chem. Soc. 2002, 124, 11064-11072. (Pubitemid 35025665)
41. Muller, G. Luminescent chiral lanthanide(iii) complexes as potential molecular probes. Dalton Trans. 2009, 9692-9707.
42. Dydio, P.; Rubay, C.; Gadzikwa, T.; Lutz, M.; Reek, J.N.H. "Cofactor"-controlled enantioselective catalysis. J. Am. Chem. Soc. 2011, 133, 17176-17179.
43. Akine, S.; Hotate, S.; Nabeshima, T. A Molecular leverage for helicity control and helix inversion. J. Am. Chem. Soc. 2011, 133, 13868-13871.
44. Carney, P.; Lopez, S.; Mickley, A.; Grinberg, K.; Zhang, W.; Dai, Z. Multimode selective detection of mercury by chiroptical fluorescent sensors based on methionine/cysteine. Chirality 2011, 23, 916-920.
45. Sanji, T.; Sato, Y.; Kato, N.; Tanaka, M. Solvophobically and metal-coordination-driven chirality induction in poly(m-phenylenedisilanylene). Macromolecules 2007, 40, 4747-4749. (Pubitemid 47169884)
46. Otsuka, I.; Sakai, R.; Satoh, T.; Kakuchi, R.; Kaga, H.; Kakuchi, T. Metal-cation-induced chiroptical switching for poly(phenylacetylene) bearing a macromolecular ionophore as a graft chain. J. Polymer Sci. A: Polymer Chem. 2005, 43, 5855-5863. (Pubitemid 43080574)
47. Pagel, K.; Vagt, T.; Kohajda, T.; Koksch, B. From alpha-helix to beta-sheet - A reversible metal ion induced peptide secondary structure switch. Org. Biomol. Chem. 2005, 3, 2500-2502. (Pubitemid 41068482)
48. Shirotani, D.; Suzuki, T.; Kaizaki, S. Novel configurational structures of sodium tetrakis(3- heptafluorobutylryl-(+)-camphorato) Ln(III) complexes with a trapped Na+ by Na+FC interactions in the solid state and in solution. Inorg. Chem. 2006, 45, 6111-6113.
49. Gregolinski, J.; Starynowicz, P.; Hua, K.T.; Lunkley, J.L.; Muller, G.; Lisowski, J. Helical lanthanide(III) complexes with chiral nonaaza macrocycle. J. Am. Chem. Soc. 2008, 130, 17761-17773.
50. Barcena, H.S.; Liu, B.; Mirkin, M.V.; Canary, J.W. An electrochiroptical molecular switch: Mechanistic and kinetic studies. Inorg. Chem. 2005, 44, 7652-7660. (Pubitemid 41540853)
51. Das, D.; Dai, Z.; Holmes, A.E.; Canary, J.W. Exploring the scope of redox-triggered chiroptical switches: Syntheses, X-ray structures and circular dichroism of cobalt and nickel complexes of N,N-bis(arylmethyl)methionine derivatives. Chirality 2008, 20, 585-591. (Pubitemid 351303999)
52. Zahn, S.; Das, D.; Canary, J.W. Redox-induced ligand reorganization and helicity inversion in copper complexes of N,N-dialkylmethionine derivatives. Inorg. Chem. 2006, 45, 6056-6063.
53. Holmes, A.E.; Zahn, S.; Canary, J.W. Synthesis and circular dichroism studies of N,N-bis(2- quinolylmethyl)amino acid Cu(II) complexes: Determination of absolute configuration and enantiomeric excess by the exciton coupling method. Chirality 2002, 14, 471-477. (Pubitemid 34754679)
54. Catagnetto, J.M.; Canary, J.W. A chiroptically enhanced fluorescent chemosensor. Chem. Commun. 1998, 203-204. (Pubitemid 128675182)
55. Lee, J.; Dai, Z. Pace University, New York, NY, USA, Unpublished work, 2012.
56. Nehira, T.; Parish, C.A.; Jockusch, S.; Turro, N.J.; Nakanishi, K.; Berova, N. Fluoresencedetected exciton-coupled circular dichroism: Scope and limitation in structural studies of organic molecules. J. Am. Chem. Soc. 1999, 121, 8681-8691. (Pubitemid 29461515)
57. Dai, Z.; Proni, G.; Mancheno, D.; Karimi, S.; Berova, N.; Canary, J.W. Detection of zinc ion by differential circularly polarized fluorescence excitation. J. Am. Chem. Soc. 2004, 126, 11760-11761. (Pubitemid 39298303)
58. Hassey, R.; Swain, E.J.; Hammer, N.I.; Venkataraman, D.; Barnes, M.D. Probing the chiroptical response of a single molecule. Science 2006, 314, 1437-1439. (Pubitemid 44871946)
59. Yamada, T.; Shinoda, S.; Sugimoto, H.; Uenishi, J.; Tsukube, H. Luminescent lanthanide complexes with stereo-controlled tris(2-pyridylmethyl) amine ligands: Chirality effects on lanthalide complexation and luminescent properties. Inorg. Chem. 2003, 42, 7932-7937.
60. Masaki, M.E.; Paul, D.; Nakamura, R.; Kataoka, Y.; Shinoda, S.; Tsukube, H. Chiral tripode approach toward multiple anion sensing with lanthanide complexes. Tetrahedron 2009, 65, 2525-2530.
61. Miyake, H.; Yoshida, K.; Sugimoto, H.; Tsukube, H. Dynamic helicity inversion by achiral anion stimulus in synthetic labile cobalt(II) complex. J. Am. Chem. Soc. 2004, 126, 6524-6525. (Pubitemid 38697332)
62. Meudtner, R.M.; Hecht, S. Helicity Inversion in Responsive foldamers induced by achiral halide ion guests. Angew. Chem. Int. Ed. 2008, 47, 4926-4930.
63. Lv, J.; Zhang, L.; Zhou, Y.; Nie, Z.; Luo, S.; Cheng, J.-P. Asymmetric binary acid catalysis: A regioselectivity switch between enantioselective 1,2- and 1,4-addition through different counteranions of InIII. Angew. Chem. Int. Ed. 2011, 50, 6610-6614.
64. Borovkov, V.V.; Hembury, G.A.; Inoue, Y. The origin of solvent-controlled supramolecular chirality switching in a bis(zinc porphyrin) system. Angew. Chem. Int. Ed. 2003, 42, 5310-5314. (Pubitemid 37462641)
65. Hutin, M.; Nitschke, J. Solvent-tunable inversion of chirality transfer from carbon to copper. Chem. Commun. 2006, 16, 1724-1726. (Pubitemid 43793251)
66. Gregolinski, J.; Slepokura, K.; Lisowski, J. Lanthanide complexes of the chiral hexaaza macrocycle and its meso-type isomer: Solvent-controlled helicity inversion. Inorg. Chem. 2007, 46, 7923-7934.
67. Lama, M.; Mamula, O.; Kottas, G.S.; De Cola, L.; Stoeckli-Evans, H.; Shova, S. Enantiopure, supramolecular helices containing 3D tetranuclear lanthanide(III) arrays: Synthesis, structure, properties and solvent-driven trinuclear/tetranuclear interconversion. Inorg. Chem. 2008, 47, 8000-8015.
68. Nakako, H.; Nomura, R.; Masuda, T. Helix inversion of poly(propiolic esters). Macromolecules 2001, 34, 1496-1502. (Pubitemid 32254000)
69. Kawagoe, Y.; Fujiki, M.; Nakano, Y. Limonene magic: Noncovalent molecular chirality transfer leading to ambidextrous circularly polarised luminescent π-conjugated polymers. New J. Chem. 2010, 34, 637-647.
70. Tang, H.-Z.; Boyle, P.D.; Novak, B.M. Chiroptical switching polyguanidine synthesized by helixsense- selective polymerization using [(R)-3,3'-Dibromo-2, 2'-binaphthoxy](di-tert-butoxy)titanium(IV) catalyst. J. Am. Chem. Soc. 2005, 127, 2136-2142. (Pubitemid 40270516)
71. Yamada, T.; Nagata, Y.; Suginome, M. Non-hydrogen-bonding-based, solvent-dependent helix inversion between pure P-helix and pure M-helix in poly(quinoxaline-2,3-diyl)s bearing chiral side chains. Chem. Commun. 2010, 46, 4914-4916.
72. Yamamoto, T.; Yamada, T.; Nagata, Y.; Suginome, M. High-molecular-weight polyquinoxalinebased helically chiral phosphine (PQXphos) as chirality-switchable, reusable, and highly enantioselective monodentate ligand in catalytic asymmetric hydrosilylation of styrenes. J. Am. Chem. Soc. 2010, 132, 7899-7901.
73. Yamamoto, T.; Akai, Y.; Nagata, Y.; Suginome, M. Highly enantioselective synthesis of axially chiral biarylphosphonates: Asymmetric Suzuki-Miyaura coupling using high-molecular-weight, helically chiral polyquinoxaline-based phosphines. Angew. Chem. Int. Ed. 2011, 50, 8844-8847.
74. Tian, X.; Cassani, C.; Liu, Y.; Moran, A.; Urakawa, A.; Galzerano, P.; Arceo, E.; Melchiorre, P. Diastereodivergent asymmetric sulfa-Michael additions of α-branched enones using a single chiral organic catalyst. J. Am. Chem. Soc. 2011, 133, 17934-17941.
75. Zelikovich, L.; Libman, J.; Shanzer, A. Molecular redox switches based on chemical triggering of iron translocation in triple-stranded helical complexes. Nature 1995, 374, 790-792.
76. Company, A.; Guell, M.; Popa, D.; Benet-Buchholz, J.; Parella, T.; Fontrodona, X.; Llobet, A.; Miquel Sola, M.; Xavi Ribas, X.; Luis, J.M.; Costas, M. Redox-controlled molecular flipper based on a chiral Cu complex. Inorg. Chem. 2006, 45, 9643-9645.
77. Li, D.; Wang, Z.Y.; Ma, D. Electrically-controlled near-infrared chiroptical switching of enantiomeric dinuclear ruthenium complexes. Chem. Commun. 2009, 1529-1531.
78. Yamaguchi, S.; Katoh, T.; Shinokubo, H.; Osuka, A. Pt(II)- and Pt(IV)-bridged cofacial diporphyrins via carbon-transition metal σ-bonds. J. Am. Chem. Soc. 2008, 130, 14440-14441.
79. Zahn, S.; Canary, J.W. Redox-switched exciton-coupled circular dichroism: A novel strategy for binary molecular switching. Angew. Chem. Int. Ed. 1998, 37, 305-307.
80. Zhang, J.; Canary, J.W. Redox-triggered interconversion between piperidine chair conformations in a Cu(I/II) complex. Org. Lett. 2006, 8, 3907-3910. (Pubitemid 44432817)
81. Zahn, S.; Proni, G.; Spada, G.P.; Canary, J.W. Supramolecular detection of metal ion binding: Ligand conformational control of cholesteric induction in nematic liquid crystalline phases. Chem.-Eur. J. 2001, 7, 88-93.
82. Zahn, S.; Canary, J.W. Absolute configurations of N,N-dialkyl alpha-amino acids and beta-amino alcohols from exciton-coupled circular dichroism spectra of Cu(II) complexes. Org. Lett. 1999, 1, 861-864.
83. Zahn, S.; Canary, J.W. Electron-induced inversion of helical chirality in copper complexes of N,N-dialkylmethionines. Science 2000, 288, 1404-1407. (Pubitemid 30366323)
84. Holmes, A.E.; Das, D.; Canary, J.W. Chelation-enhanced circular dichroism of tripodal bisporphyrin ligands. J. Am. Chem. Soc. 2007, 129, 1506-1507.
85. Barcena, H.S.; Holmes, A.E.; Canary, J.W. Inversion of helicity in propeller shaped molecules derived from S-methylcysteine and methioninol. Org. Lett. 2003, 709-711. (Pubitemid 37141085)
86. Goto, H.; Yashima, E. Electron-induced switching of the supramolecular chirality of optically active polythiophene aggregates. J. Am. Chem. Soc. 2002, 124, 7943-7949. (Pubitemid 34759954)
87. Ohta, E.; Sato, H.; Ando, S.; Kosaka, A.; Fukushima, T.; Hashizume, D.; Yamasaki, M.; Hasegawa, K.; Muraoka, A.; Ushiyama, H.; et al. Redox-responsive molecular helices with highly condensed π-clouds. Nat. Chem. 2011, 3, 68-73.
88. Gregson, C.K.A.; Gibson, V.C.; Long, N.J.; Marshall, E.L.; Oxford, P.J.; White, A.J.P. Redox control within single-site polymerization catalysts. J. Am. Chem. Soc. 2006, 128, 7410-7411. (Pubitemid 43877493)
89. Iida, H.; Mizoguchi, T.; Oh, S.-D.; Yashima, E. Redox-triggered switching of helical chirality of poly(phenylacetylene)s bearing riboflavin pendants. Polymer Chem. 2010, 1, 841-848.
90. Lorkovic, I.M.; Duff, R.R.; Wrighton, M.S. Use of the redox-active ligand 1,1'- bis(diphenylphosphino)cobaltocene to reversibly alter the rate of the rhodium(I)-catalyzed reduction and isomerization of ketones and alkenes. J. Am. Chem. Soc. 1995, 117, 3617-3618.
91. Wiggins, K.M.; Hudnall, T.W.; Shen, Q.; Kryger, M.J.; Moore, J.S.; Bielawski, C.W. Mechanical reconfiguration of stereoisomers. J. Am. Chem. Soc. 2010, 132, 3256-3257.
92. Tashiro, R.; Sugiyama, H. Biomolecule-based switching devices that respond inversely to thermal stimuli. J. Am. Chem. Soc. 2005, 127, 2094-2097. (Pubitemid 40270511)
93. Huang, Z.-Z.; Kang, Y.-B.; Zhou, J.; Ye, M.-C.; Tang, Y. Diastereoselectivity-switchable and highly enantioselective 1,3-dipolar cycloaddition of nitrones to alkylidene malonates. Org. Lett. 2004, 6, 1677-1679. (Pubitemid 38698479)
94. Ben-Asuly, A.; Tzur, E.; Diesendruck, C.E.; Sigalov, M.; Goldberg, I.; Lemcoff, N.G. A thermally switchable latent ruthenium olefin metathesis catalyst. Organometallics 2008, 27, 811-813. (Pubitemid 351526748)
95. Mathews, M.; Tamaoki, N. Planar chiral azobenzenophanes as chiroptic switches for photon mode reversible reflection color control in induced chiral nematic liquid crystals. J. Am. Chem. Soc. 2008, 130, 11409-11416.
96. Zhang, W.; Yoshida, K.; Fujiki, M.; Zhu, X. Unpolarized-light-driven amplified chiroptical modulation between chiral aggregation and achiral disaggregation of an azobenzene-alt-fluorene copolymer in limonene. Macromolecules 2011, 44, 5105-5111.
97. Stoll, R.S.; Peters, M.V.; Kuhn, A.; Heiles, S.; Goddard, R.; Bühl, M.; Thiele, C.M.; Hecht, S. Photoswitchable catalysts: Correlating structure and conformational dynamics with reactivity by a combined experimental and computational approach. J. Am. Chem. Soc. 2008, 131, 357-367.
98. Wang, J.; Feringa, B.L. Dynamic control of chiral space in a catalytic asymmetric reaction using a molecular motor. Science 2011, 331, 1429-1432.