Structures and encapsulation motifs of functional molecules probed by laser spectroscopic and theoretical methods

Sensors

Volumn 10, Issue 4, 2010, Pages 3519-3548

  Kusaka, Ryoji ^a   Inokuchi, Yoshiya ^a   Xantheas, Sotiris S ^b   Ebata, Takayuki ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

^b PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

Author keywords

Calixarene; Crown ether; Host guest complex; Laser spectroscopy; Supersonic jet

Indexed keywords

CALIXARENES; COMPUTATIONAL STUDIES; FIRST PRINCIPLES ELECTRONIC STRUCTURE; HOST GUEST COMPLEXES; HYDRATION INTERACTION; LASER INDUCED FLUORESCENCE; RESONANCE-ENHANCED MULTIPHOTON IONIZATION; SUPERSONIC JETS;

CROWN ETHERS; ELECTRONIC STRUCTURE; ETHERS; LASER SPECTROSCOPY; MOLECULES; PHOTOIONIZATION; SPECTROSCOPIC ANALYSIS;

SUPERSONIC AERODYNAMICS;

EID: 77951707248     PISSN: 14248220     EISSN: None     Source Type: Journal    
DOI: 10.3390/s100403519     Document Type: Review

References (56)

1. Gokel G.W. Crown Ethers and Cryptands; Royal Society of Chemistry: Cambridge UK 1991.
2. Dobler M. Ionophores and their Structures; Wiley-Interscience: New York NY USA 1981.
3. Gutsche C.D. "Calixarenes" in Monographs in Supramolecular Chemistry Stoddart J.F. Ed.; Royal Society of Chemistry: Cambridge UK 1989.
4. Cram D.J.; Cram J.M. "Container molecules and their guests" in Monographss in Supramolecular Chemistry Stoddart J.F. ed.; Royal Society of Chemistry: Cambridge UK 1994.
5. Gutsche C.D. "Calixarenes revisited" in Monographs in Supramolecular Chemistry Stoddart J.F. Ed.; Royal Society of Chemistry: Cambridge UK 1998.
6. Stuart A.M.; Vidal J.A. Perfluoroalkylated 4,13-diaza-18-crown-6 ethers: synthesis phasetransfer catalysis and recycling studies. J. Org. Chem. 2007 72 3735-3740.
7. Chekholov A.N. (18-crown-6)potassium tris(thiocyanato)nickelate(II): Synthesis and crystal structure. Russ. J. Coord. Chem. 2008 34 434-437.
8. Atwood J.L.; Koutsoantonis G.A.; Raston C.L. Purification of C60 and C70 by selective complexation with calixarenes. Nature 1994 368 229.
9. Suzuki T.; Nakashima K.; Shinkai S. Very Convenient and efficient purification method for fullerene (C60) with 5,11,17,23,29,35,41,47-Octa-tert-butylcalix[8]arene-49,50,51,52,53,54,55,56-octol. Chem. Lett. 1994 23 699.
10. Izatt R.M.; Rytting J.H.; Nelson D.P.; Haymore B.L.; Christensen J.J. Binding of alkali metal ions by cyclic polyethers: significance in ion transport processes. Science 1969 164 443.
11. Izatt R.M.; Nelson D.P.; Rytting J.H.; Haymore B.L.; Christensen J.J. Calorimetric study of the interaction in aqueous solution of several uni- and bivalent metal ions with the cyclic polyether dicyclohexyl-18-crown-6 at 10,25 and 40.deg. J. Am. Chem. Soc. 1971 93 1619.
12. Izatt R.M.; Terry R.E.; Haymore B.L.; Hansen L.D.; Dalley N.K.; Avondet A.G.; Christensen J.J. Calorimetric titration study of the interaction of several uni- and bivalent cations with 15-crown-5 18-crown-6 and two isomers of dicyclohexo-18-crown-6 in aqueous solution at 25.degree.C and.mu. = 0.1. J. Am. Chem. Soc. 1976 98 7620.
13. Izatt R.M.; Terry R.E.; Nelson D.P.; Chan Y.; Eatough D.J.; Bradshaw J.S.; Hansen L.D.; Christensen J.J. Calorimetric titration study of the interaction of some uni- and bivalent cations with benzo-15-crown-5 18-crown-6 dibenzo-24-crown-8 and dibenzo-27-crown-9 in methanolwater solvents at 25.degree.C and.mu. = 0.1. J. Am. Chem. Soc. 1976 98 7626.
14. Lamb J.D.; Izatt R.M.; Swain C.S.; Christensen J.J. A systematic study of the effect of macrocycle ring size and donor atom type on the log K,.DELTA.H and T.DELTA.S of reactions at 25.degree.C in methanol of mono- and divalent cations with crown ethers. J. Am. Chem. Soc.1980 102 475.
15. Pedersen C.J.; Frensdorff H.K. Macrocyclic polyethers and their complexes Angew. Chem. Int. Ed. 1972 11 16.
16. Glendening E.D.; Feller D.; Thompson M.A. An Ab Initio Investigation of the Structure and Alkali Metal Cation Selectivity of 18-Crown-6. J. Am. Chem. Soc. 1994 116 10657.
17. More M.B.; Ray D.; Armentrout P.D. Intrinsic affinities of alkali cations for 15-crown-5 and 18-crown-6: bond dissociation energies of gas-phase M+-crown ether complexes. J. Am. Chem. Soc. 1999 121 417-423.
18. Hill S.E.; Feller D. Theoretical study of cation/ether complexes: 15-crown-5 and its alkali metal complexes. Int. J. Mass Spectrom. 2000 201 41.
19. Peiris D.M.; Yang Y.; Ramanathan R.; Williams K.R.; Watson C.; Eyler J.R. Infrared multiphoton dissociation of electrosprayed crown ether complexes. Int. J. Mass Spectrom. Ion Process. 1996 157/158 365.
20. Anderson J.D.; Paulsen E.S.; Dearden D. Alkali metal binding energies of dibenzo-18-crown-6: experimental and computational results. Int. J. Mass Spectrom. 2003 227 63.
21. Armentrout P.B. Cation-ether complexes in the gas phase: thermodynamic insight into molecular recognition. Int. J. Mass Spectrom. 1999 193 227.
22. Feller D. Ab Initio Study of M+:18-Crown-6 Microsolvation. J. Phys. Chem. A 1997 101 2723-2731.
23. Rodriguez J.D.; Lisy J.M. Infrared spectroscopy of gas-phase hydrated K+:18-crown-6 complexes: Evidence for high energy conformer trapping using the argon tagging method. Int. J. Mass. spectrom. 2009 283 135-139.
24. Rodriguez J.D.; Lisy J.M. Infrared spectroscopy of multiply charged metal ions: methanolsolvated divalent manganese 18-crown-6 ether systems. J. Phys. Chem. A 2009 113 6462-6467.
25. Rodriguez J.D.; Vaden T.D.; Lisy J.M. Infrared spectroscopy of ionophore-model systems: hydrated alkali metal ion 18-crown-6 ether complexes. J. Am. Chem. Soc. 2009 131 17277-17285.
26. Shubert V.A.; Zwier T.S. IR-IR-UV Hole-burning: conformation specific IR spectra in the face of UV spectral overlap. J. Phys. Chem. A 2007 111 13283-13286.
27. Shubert V.A.; James III W.H.; Zwier T.S. Jet-cooled electronic and vibrational spectroscopy of crown ethers: benzo-15-crown-5 ether and 4′ -amino-benzo-15-crown-5 ether. J. Phys. Chem. A 2009 113 8055-8066.
28. 2O)n n = 1 2. J. Phys. Chem. A 2009 113 8067-8079.
29. Kusaka R.; Inokuchi Y.; Ebata T. Laser spectroscopic study on the conformations and the hydrated structures of benzo-18-crown-6-ether and dibenzo-18-crown-6-ether in supersonic jets. Phys. Chem. Chem. Phys. 2007 9 4452-4459.
30. Kusaka R.; Inokuchi Y.; Ebata T. Structure of hydrated clusters of dibenzo-18-crown-6-ether in a supersonic jet-encapsulation of water molecules in the crown cavity Phys. Chem. Chem. Phys. 2008 10 6238-6244.
31. Kusaka R.; Inokuchi Y.; Ebata T. Water-mediated conformer optimization in benzo-18-crown-6-ether/water system. Phys. Chem. Chem. Phys. 2009 11 9132-9140.
32. Ebata T.; Hodono Y.; Ito T.; Inokuchi Y. Electronic spectra of jet-cooled calix[4]arene and its van der Waals clusters: Encapsulation of a neutral atom in a molecular bowl. J. Chem. Phys. 2007 126 141101.
33. 2O) cluster: The world's smallest cup of water J. Phys. Chem. A 2010 114 2967.
34. Ebata T. Study on the structure and vibrational dynamics of functional molecules and molecular clusters by double resonance vibrational spectroscopy. Bull. Chem. Soc. Jpn. 2009 82 127.
35. Frisch M.J.; Trucks G.W.; Schlegel H.B.; Scuseria G.E.; Robb M.A.; Cheesman J.R.; Montgomery Jr. J.A.; Vreven T.; Kudin K.N.; Burant J.C.; Millam J.M.; Iyengar S.S.; Tomasi J.; Barone V.; Munnucci B.; Cossi M.; Scalmani G.; Rega N.; Petersson G.A.; Nakatsuji H.; Hada M.; Ehara M.; Toyota K.; Fukuda R.; Hasegawa J.; Ishida M.; Nakajima T.; Honda Y.; Kitao O.; Nakai H.; Klene M.; Li X.; Knox J.E.; Hratchian H.P.; Cross J.B.; Bakken V.; Asamo C.; Jaramillo J.; Gomperts R.; Stratmann R.E.; Yazyev O.; Ausitin A.J.; Cammi R.; Pomelli C.; Ochterski J.W.; Ayala P.Y.; Morokuma K.; Voth G.A.; Salvador P.; Dannenberg J.J.; Zakrzewski V.G.; Dapprich S.; Daniels A.D.; Strain M.C.; Farkas O.; Malick D.K.; Rabuck A.D.; Raghavachari K.; Foresman J.B.; Ortiz J.V.; Cui Q.; Baboul A.G.; Clifford S.; Cioslowski J.; Stefanov B.B.; Liu G.; Liashenko A.; Piskorz P.; Komaromi I.; Martin R.L.; Fox D.J.; Keith T.; Al-Laham M.A.; Peng C.Y.; Nanayakkara A.; Challacombe M.; Gill P.M. W.; Johnson B.; Chen W.; Wong M.W.; Conzalez C.; Pople J.A. Gaussian 03 Revision D.02, Gaussian Inc.: Wallingford CT USA 2004.
36. Møller C.; Plesset M.S. Note on an approximation treatment for many-electron systems. Phys. Rev. 1934 46 618.
37. Dunning Jr. T.H. Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen. J. Chem. Phys. 1989 90 1007.
38. Kendall R.A.; Dunning Jr. T.H.; Harrison R.J. Electron affinities of the first-row atoms revisited. Systematic basis sets and wave functions. J. Chem. Phys. 1992 96 6796.
39. Kendall R.A.; Aprà E.; Bernholdt D.E.; Bylaska E.J.; Dupuis M.; Fann G.I.; Harrison R.J.; Ju J.; Nichols J.A.; Nieplocha J.; Straatsma T.P.; Windus T.L.; Wong A.T. High performance computational chemistry: An overview of NWChem a distributed parallel application Comp. Phys. Comm. 2000 128 260-283; High Performance Computational Chemistry Group (2003) NWChem A Computational Chemistry Package for Parallel Computers Version 4.6. Pacific Northwest National Laboratory: Richland WA 99352 USA.
40. Hehre W.J.; Ditchfield R.; Pople J.A. Self-consistent molecular orbital methods. XII. Further extensions of Gaussian-type basis sets for use in molecular orbital studies of organic molecules. J. Chem. Phys. 1972 56 2257.
41. Boys S.F.; Bernardi F. The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Mol. Phys. 1970 19 553.
42. Xantheas S.S. On the importance of the fragment relaxation energy terms in the estimation of the basis set superposition error correction to the intermolecular interaction energy. J. Chem. Phys. 1996 104 8821.
43. Bright D.; Truter M.R. Crystal structures of complexes between alkali-metal salts and cyclic polyethers. Part I. Complex formed between rubidium sodium isothiocyanate and 2,3,11,12-dibenzo-1,4,7,10,13,16-hexaoxocyclo-octadeca-2,11-diene ('dibenzo-18-crown-6'). J. Chem. Soc. B 1970 8 1544.
44. Müller A.; Talbot F.; Leutwyler S. S1/S2 exciton splitting in the (2-pyridone)2 dimer. J. Chem. Phys. 2002 116 2836.
45. Wessel J.E.; Syage J.A. Excitonic interactions in naphthalene clusters J. Phys. Chem. 1990 94 737.
46. Herzberg G. Molecular Spectra And Molecular Structure Volume II. Infrared and Raman Spectra of Polyatomic Molecules Van Nostrand Reinhold Company: New York NY USA 1945.
47. Yi J.Y.; Ribblett J.W.; Pratt D.W. Rotationally resolved electronic spectra of 1,2-dimethoxybenzene and the 1,2-dimethoxybenzene-water complex. J. Phys. Chem. A 2005 109 9456-9464.
48. Bühl M.; Wipff G. Hydronium Ion complex of 18-crown-6: where are the protons? a density functional study of static and dynamic properties. J. Am. Chem. Soc. 2002 124 4473-4480.
49. Goutev N.; Matsuura H. Hydrogen Bonding in Chloroform Solutions of Ethylenedioxy Ethers. Spectroscopic Evidence of Bifurcated Hydrogen Bonds. J. Phys. Chem. A 2001 105 4741-4748.
50. Hang Z.S.; Miller R.E. High-resolution near-infrared spectroscopy of water dimer J. Chem. Phys. 1989 91 6613.
51. Fukuhara K.; Tachikake M.; Matsumoto S.; Matsuura H. Raman spectroscopic study of the hydrates of 18-crown-6. J. Phys. Chem. 1995 99 8617-8623.
52. Ebata T.; Nagao K.; Mikami N. Mode-dependent anharmonic coupling between OH stretching and intermolecular vibrations of the hydrogen-bonded clusters of phenol. Chem. Phys. 1998 231 199-204.
53. Nibu Y.; Marui R.; Shimada H. Infrared spectroscopy of hydrogen-bonded 2-fluoropyridine-water clusters in supersonic jets. J. Phys. Chem. A 2006 110 9627-9632.
54. T.; Hontama N.; Inokuchi Y.; Haino T.; Xantheas S.S. Encapsulation of Arn complexes by calix[4]arene: endo- vs. exo-complexes. Phys. Chem. Chem. Phys. in press.
55. Xantheas S.S. Cooperativity and hydrogen bonding network in water clusters. Chem. Phys. 2000 258 225.
56. 2O)n Structures. Science 1994 265 75-79.