Investigation on CD inversion at visible region caused by a tilt of the π-conjugated substituent: Theoretical and experimental approaches by using an asymmetric framework of diarylethene annulated isomer

Journal of Physical Chemistry A

Volumn 118, Issue 6, 2014, Pages 1084-1093

  Hirose, Takashi ^a   Inoue, Yuki ^a   Hasegawa, Jun Ya ^b   Higashiguchi, Kenji ^a,c   Matsuda, Kenji ^a  

^a KYOTO UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; LIGHT RELATED PHENOMENA; PHOTOCHEMISTRY; QUANTUM THEORY; STEREOISOMERISM;

CIRCULAR DICHROISM; HYDROCARBONS, AROMATIC; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OPTICAL PROCESSES; PHOTOCHEMICAL PROCESSES; QUANTUM THEORY; STEREOISOMERISM;

EID: 84894093257     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp4122694     Document Type: Article

References (35)

1. Johnson, W. C., Jr. Secondary Structure of Proteins through Circular Dichroism Spectroscopy Ann. Rev. Biophys. Chem. 1988, 17, 145-166
2. Kelly, S. M.; Jess, T. J.; Price, N. C. How to Study Proteins by Circular Dichroism Biochim. Biophys. Acta 2005, 1751, 119-139 (Pubitemid 41112231)
3. Miles, A. J.; Wallace, B. A. Synchrotron Radiation Circular Dichroism Spectroscopy of Proteins and Applications in Structural and Functional Genomics Chem. Soc. Rev. 2006, 35, 39-51 (Pubitemid 43485012)
4. Ranjbar, B.; Gill, P. Circular Dichroism Techniques: Biomolecular and Nanostructural Analyses-A Review Chem. Biol. Drug Des. 2009, 74, 101-120
5. Gray, D. M.; Ratliff, R. L.; Vaughan, M. R. Circular Dichroism Spectroscopy of DNA Methods Enzymol. 1992, 211, 389-406
6. Woody, R. W. Circular Dichroism Methods Enzymol. 1995, 246, 34-71
7. Berova, N.; Di Bari, L.; Pescitelli, G. Application of Electronic Circular Dichroism in Configurational and Conformational Analysis of Organic Compounds Chem. Soc. Rev. 2007, 36, 914-931
8. Łysek, R.; Borsuk, K.; Chmielewski, M.; KałuzÌ ‡a, Z.; Urbańczyk-Lipkowska, Z.; Klimek, A.; Frelek, J. 5-Dethia-5-oxacephams: Toward Correlation of Absolute Configuration and Chiroptical Properties J. Org. Chem. 2002, 67, 1472-1479 (Pubitemid 34211589)
9. Scott, A. I.; Wrixon, A. D. A Symmetry Rule for Chiral Olefins Tetrahedron 1970, 26, 3695-3715
10. Moscowitz, A.; Charney, E.; Weiss, U.; Ziffer, H. Optical Activity in Skewed Dienes J. Am. Chem. Soc. 1961, 83, 4661-4663
11. Moscowitz, A.; Mislow, K.; Glass, M. A. W.; Dierassi, C. Optical Rotatory Dispersion Associated with Dissymmetric Non-conjugated Chromophores. An Extension of the Octant Rule J. Am. Chem. Soc. 1962, 84, 1945-1955
12. Moffitt, W.; Woodward, R. B.; Moscowitz, A.; Klyne, W.; Djerassi, C. Structure and the Optical Rotatory Dispersion of Saturated Ketones J. Am. Chem. Soc. 1961, 83, 4013-4018
13. Klyne, W.; Kirk, D. N. The Signs of Chiral Properties: Suggested Terms "Consignate" and "Dissignate Tetrahedron Lett. 1973, 14, 1483-1486
14. Crawfold, T. D.; Tam, M. C.; Abrams, M. L. The Current State of Ab Initio Calculations of Optical Rotation and Electronic Circular Dichroism Spectra. J Phys. Chem. A 2007, 111, 12057-12068 (Pubitemid 350275434)
15. Diedrich, C.; Grimme, S. Systematic Investigation of Modern Quantum Chemical Methods to Predict Electronic Circular Dichroism Spectra J. Phys. Chem. A 2003, 107, 2524-2539
16. Furche, F.; Ahlrichs, R.; Wachsmann, C.; Wever, E.; Sobanski, A.; Vögtle, F.; Grimme, S. Circular Dichroism of Helicenes Investigated by Time-Dependent Density Functional Theory J. Am. Chem. Soc. 2000, 122, 1717-1724 (Pubitemid 30134217)
17. Laurent, A. D.; Jacquemin, D. TD-DFT Benchmarks: A Review Int. J. Quantum Chem. 2013, 113, 2019-2039 and references therein.
18. Nakano, Y.; Hirose, T.; Stals, P. J. M.; Meijer, E. W.; Palmans, A. R. A. Conformation Analysis of Supramolecular Polymerization Process of Disc-Like Molecules Chem. Sci. 2012, 3, 148-155
19. Stephens, P. J.; McCann, D. M.; Butkus, E.; Stončius, S.; Cheeseman, J. R.; Frisch, M. J. Determination of Absolute Configuration Using Concerted ab Initio DFT Calculations of Electronic Circular Dichroism and Optical Rotation; Bicyclo[3.3.1]nonane Diones J. Org. Chem. 2004, 69, 1948-1958 and references therein. (Pubitemid 38366659)
20. Hirose, T.; Hasegawa, J.; Matsuda, K. Theoretical Investigation on the Origin of the CD Signal Reversal for the Closed-ring Isomer of Diarylethene with Peripherical π-Conjugated Substituents Chem. Lett. 2010, 39, 516-517
21. Irie, M.; Lifka, T.; Uchida, K.; Kobatake, S.; Shindo, Y. Fatigue Resistant Properties of Photochromic Dithienylethenes: By-Product Formation Chem. Commun. 1999, 747-750
22. Patel, P. D.; Mikhailov, I. A.; Belfield, K. D.; Masunov, A. E. Theoretical Study of Photochromic Compounds, Part 2: Thermal Mechanism for Byproduct Formation and Fatigue Resistance of Diarylethenes Used as Data Storage Materials Int. J. Quantum Chem. 2009, 109, 3711-3722
23. Higashiguchi, K.; Matsuda, K.; Kobatake, S.; Yamada, T.; Kawai, T.; Irie, M. Fatigue Mechanism of Photochromic 1,2-Bis(2,5-dimethyl-3-thienyl) perfluorocyclopentene Bull. Chem. Soc. Jpn. 2000, 73, 2389-2394
24. 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)
25. Cyphersmith, A.; Surampudi, S.; Casey, M. J.; Jankowski, K.; Venkataraman, D.; Barnes, M. D. Chiroptical Dissymmetries in Fluorescence Excitation from Single Molecules of (M-2) Helicene Dimers J. Phys. Chem. A 2012, 116, 5349-5352
26. Liu, G.; Pu, S.; Wang, R. Photochromism of Asymmetrical Diarylethenes with a Pyrrole Unit: Effects of Aromatic Stabilization Energies of Aryl Rings Org. Lett. 2013, 15, 980-983
27. Liu, G.; Pu, S.; Wang, X. Synthesis and the Effect of Substituent Position upon Unsymmetrical Isomeric Diarylethenes Bearing a Pyrrole Unit J. Photochem. Photobiol. A: Chem. 2010, 214, 230-240
28. Pu, S.; Liu, G.; Shen, L.; Xu, J. Efficient Synthesis and Properties of Isomeric Photochromic Diarylethenes Having a Pyrrole Unit Org. Lett. 2007, 9, 2139-2142
29. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy: Exciton Coupling in Organic Stereochemistry: University Science Books: Mill Valley, CA, 1983.
30. Cordell, F. R.; Boggs, J. E. Structure and Degree of Aromatic Character in Furan, Pyrrole, and Thiophene THEOCHEM 1981, 85, 163-178
31. a-Modulation and Gated Photochromic Properties of a Novel Diarylethene Switch Eur. J. Org. Chem. 1999, 2359-2366
32. Flack, H. D.; Bernardinelli, G. Reporting and Evaluating Absolute-Structure and Absolute-Configuration Determinations J. Appl. Crystallogr. 2000, 33, 1143-1148 (Pubitemid 32182502)
33. Wakai, A.; Fukasawa, H.; Yang, C.; Mori, T.; Inoue, Y. Theoretical and Experimental Investigations of Circular Dichroism and Absolute Configuration Determination of Chiral Anthracene Photodimers J. Am. Chem. Soc. 2012, 134, 4990-4997
34. Mori, T.; Inoue, Y.; Grimme, S. Quantum Chemical Study on the Circular Dichroism Spectra and Specific Rotation of Donor-Acceptor Cyclophanes J. Phys. Chem. A 2007, 111, 7995-8006 and references therein. (Pubitemid 47310943)
35. Bringmann, G.; Bruhn, T.; Maksimenka, K.; Hemberger, Y. The Assignment of Absolute Stereostructures through Quantum Chemical Circular Dichroism Calculations Eur. J. Org. Chem. 2009, 2717-2727 and references therein