A novel spectroscopic probe for molecular chirality

Chirality

Volumn 18, Issue 3, 2006, Pages 146-158

  Ji, Na ^a,b   Shen, Yuen Ron ^a,b,c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^c 366 Le Conte Hall #7300 ^*  (United States)

Author keywords

Absolute configuration; Chiral sum frequency generation; Coupled oscillator model; Dynamic coupling model; Linear optical activity; Optically active sum frequency generation; Second order nonlinear optical effects

Indexed keywords

NAPHTHOL DERIVATIVE;

CHIRALITY; CIRCULAR DICHROISM; COMPARATIVE STUDY; CONFERENCE PAPER; FILM; FREQUENCY ANALYZER; MOLECULAR MODEL; MOLECULAR PROBE; OSCILLATION; PRIORITY JOURNAL; SENSITIVITY AND SPECIFICITY; SPECTROSCOPY; SUM FREQUENCY GENERATION; TECHNIQUE; VIBRATION;

ALGORITHMS; CHEMISTRY, PHYSICAL; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 33644687130     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20238     Document Type: Conference Paper

References (48)

1. Charney E. The molecular basis of optical activity. New York: John Wiley & Sons; 1979. 364 p.
2. Berova N, Nakanishi K, Woody RW. Circular dichroism: principles and applications. New York: John Wiley & Sons; 2002. 877 p.
3. Thompson LA, Ellman JA. Synthesis and applications of small molecule libraries. Chem Rev 1996;96(1):555-600.
4. Figeys D, Pinto D. Lab-on-a-chip: a revolution in biological and medical sciences. Anal Chem 2000;72(9):330A-335A.
5. Alberts B, Johnson A, Lewis J, Raff M, Roberts K, Walter P. Molecular biology of the cell, 4th ed. New York: Garland Science; 2002. 1616 p.
6. Shen YR. A few selected applications of surface nonlinear optical spectroscopy. Proc Natl Acad Sci U S A 1996;93(22):12104-12111.
7. Shen YR. Optical second harmonic-generation at interfaces. Annu Rev Phys Chem 1989;40:327-350.
8. Belkin MA, Kulakov TA, Ernst KH, Yan L, Shen YR. Sum-frequency vibrational spectroscopy on chiral liquids: a novel technique to probe molecular chirality. Phys Rev Lett 2000;85(21):4474-4477.
9. Belkin MA, Han SH, Wei X, Shen YR. Sum-frequency generation in chiral liquids near electronic resonance. Phys Rev Lett 2001;87(11):113001-1-113001-4.
10. Ji N, Shen YR. Optically active sum frequency generation from molecules with a chiral center: amino acids as model systems. J Am Chem Soc 2004;126(46):15008-15009.
11. Han SH, Ji N, Belkin MA, Shen YR. Sum-frequency spectroscopy of electronic resonances on a chiral surface monolayer of binaphthol. Phys Rev B 2002;66(16):165415-1-165415-6.
12. Belkin MA, Shen YR. Doubly resonant IR-UV sum-frequency vibrational spectroscopy on molecular chirality. Phys Rev Lett 2003;91(21):213907-1-213907- 4.
13. Oh-e M, Yokoyama H, Yorozuya S, Akagi K, Belkin MA, Shen YR. Sum-frequency vibrational spectroscopy of a helically structured conjugated polymer. Phys Rev Lett 2004;93(26):267402-1-267402-4.
14. Boyd RW. Nonlinear optics. Orlando, FL: Academic Press, Inc.; 1992. 439 p.
15. Shen YR. The principles of nonlinear optics. New York: John Wiley & Sons; 1984. 563 p.
16. Petrallimallow T, Wong TM, Byers JD, Yee HI, Hicks JM. Circular-dichroism spectroscopy at interfaces-a surface second harmonic-generation study. J Phys Chem 1993;97(7):1383-1388.
17. Hicks JM, Petrallimallow T, Byers JD. Consequences of chirality in second-order nonlinear spectroscopy at surfaces. Faraday Discuss 1994;99:341-357.
18. Simpson GJ. Molecular origins of the remarkable chiral sensitivity of second-order nonlinear optics. ChemPhysChem 2004;5(9):1301-1310.
19. (a) Sioncke S, Verbiest T, Persoons A. Second-order nonlinear optical properties of chiral materials. Mater Sci Eng R Rep 2003;42 (5-6):115-155.
20. (b) Similar to CD and ORD, SFG can be used to probe not only molecular chirality, but also chiral spatial arrangement of either chiral or achiral molecules, either on the surface or in the bulk.
21. (a) Barron LD. Molecular light scattering and optical activity. Cambridge, England: Cambridge University Press; 2004. 466 p.
22. (b) A fundamental difference exists between the coupled-oscillator models for linear and nonlinear optical activity: although a set of coupled harmonic oscillators arranged in a chiral fashion can have linear optical activity, they cannot generate nonlinear chiral signals in SFG, because a truly harmonic oscillator cannot respond to an external field in a nonlinear way. In other words, radiation with frequencies other than that of the input wave is not possible from a system made of harmonic oscillators. Thus, it is imperative for the coupled oscillators in the nonlinear case to be anharmonic.
23. Belkin MA, Shen YR, Flytzanis C. Coupled-oscillator model for nonlinear optical activity. Chem Phys Lett 2002;363(5-6):479-485.
24. Belkin MA, Shen YR, Harris RA. Sum-frequency vibrational spectroscopy of chiral liquids off and close to electronic resonance and the antisymmetric Raman tensor. J Chem Phys 2004;120(21):10118-10126.
25. Ji N, Shen YR. A dynamic coupling model for sum frequency chiral response from liquids composed of molecules with a chiral side chain and an achiral chromophore. J Am Chem Soc 2005;127(37):12933-12942.
26. Belkin MA, Shen YR. Nonlinear optical spectroscopy as a novel probe for molecular chirality. Int Rev Phys Chem 2005;24(2):257-299.
27. Craig DP, Thirunamachandran T. Molecular quantum electrodynamics: an introduction to radiation-molecule interactions. New York: Dover Publications, Inc.; 1998. 324 p.
28. Wang J, Chen XY, Clarke ML, Chen Z. Detection of chiral sum frequency generation vibrational spectra of proteins and peptides at interfaces in situ. Proc Natl Acad Sci U S Am 2005;102(14):4978-4983.
29. Finn MG. Emerging methods for the rapid determination of enantiomeric excess. Chirality 2002;14(7):534-540.
30. Fischer P, Buckingham AD, Beckwitt K, Wiersma DS, Wise FW. New electro-optic effect: sum-frequency generation from optically active liquids in the presence of a dc electric field. Phys Rev Lett 2003;91(17):173901-1-173901- 4.
31. Kim D. Nonlinear optical properties of atomic vapor and semi-conductors. Ph.D. thesis (in physics). Berkeley, CA: University of California, Berkeley; 1997.
32. Hanazaki I, Akimoto H. Optical rotatory power of 2,2′-dihydroxy-1, 1′-binaphthyl and related compounds. J Am Chem Soc 1972;94(12):4102-4106.
33. Maria HJ, Larson D, McCarvil ME, McGlynn SP. Electronic spectroscopy of isoelectronic molecules. 1. Nonlinear triatomic groupings containing 18 valence electrons, with comments on T1 state of the peptide linkage. Acc Chem Res 1970;3(11):368-376.
34. Katzin LI, Gulyas E. Absorption rotatory dispersion and circular dichroism studies on some hydroxy and amino acids. J Am Chem Soc 1968;90(2):247-251.
35. Fowden L, Scopes PM, Thomas RN. Optical rotatory dispersion and circular dichroism. 70. Circular dichroism of some less common amino acids. J Chem Soc C-Org 1971;5:833-840.
36. Snyder PA, Vipond PM, Johnson WC. Circular dichroism of alkyl amino acids in vacuum ultraviolet. Biopolymers 1973;12(5):975-992.
37. Matsuo K, Matsushima Y, Fukuyama T, Senba S, Gekko K. Vacuum-ultraviolet circular dichroism of amino acids as revealed by synchrotron radiation spectrophotometer. Chem Lett 2002(8):826-827.
38. Nishino H, Kosaka A, Hembury GA, Matsushima K, Inoue Y. The pH dependence of the anisotropy factors of essential amino acids. J Chem Soc Perkin Trans 2 2002;3:582-590.
39. Hohn EG, Weigang OE. Electron correlation models for optical activity. J Chem Phys 1968;48(3):1127-1137.
40. Moffitt W, Woodward RB, Moscowitz A, Klyne W, Djerassi C. Structure and optical rotatory dispersion of saturated ketones. J Am Chem Soc 1961;83(19):4013-4018.
41. Denbigh KG. The polarisabilities of bonds. I. Trans Faraday Soc 1940;36:936-948.
42. Allen GW, Armstrong RS, Aroney MJ, Pierens RK, Williams AJ. Polarizability anisotropies of C-H, C-C, C-Cl, and C-Br bonds. J Chem Soc-Faraday Trans ii 1988;84:1775-1778.
43. Amos AT, Crispin RJ. Polarizabilities of C-H and C-C bonds. J Chem Phys 1975;63(5):1890-1899.
44. (a) Lefevre RJW, Orr BJ, Ritchie GLD. Molecular polarisability. Anisotropic electron polarisability of aliphatic C-C and C-H bonds. J Chem Soc B-Phys Org 1966(3):273-280.
45. (b) The reason that C-H bonds, instead of C-C bonds, are the most effective perturbers is that the C-C bonds are not located at optimum positions as the C-H bonds.
46. Buckingham AD, Stiles PJ. Theory of natural optical activity. Acc Chem Res 1974;7(8):258-264.
47. Nafie LA. Infrared and Raman vibrational optical activity: theoretical and experimental aspects. Ann Rev Phys Chem 1997;48:357-386.
48. The BN monolayer was adsorbed at the air-water interface from the solution. There are still BN molecules in bulk water, but because the solubility of BN in water is very low (saturated at the μM level), the contribution from the small number density of BN molecules in the bulk to the OA-SFG signal is negligible.