The entropic enlightenment of organic photochemistry: Strategic modifications of intrinsic decay pathways using an information-based approach

Photochemical and Photobiological Sciences

Volumn 9, Issue 12, 2010, Pages 1574-1588

  García Garibay, Miguel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78649617728     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c0pp00248h     Document Type: Article

References (51)

1. G. Ciamician The, photochemistry of the future Science 1912 36 385
2. N. Armaroli V. Balzani The, future of energy supply: challenges and opportunities Angew. Chem., Int. Ed. 2007 46 52
3. J. Michl, V. Bonaci-Koutecky, Electronic, Aspects of Organic Photochemistry, Wiley Interscience, New York, 1990
4. H. D. Roth The, beginnings of organic photochemistry Angew. Chem., Int. Ed. Engl. 1989 28 1193
5. D. C. Neckers, Selected, papers in photochemistry SPIE Optical Engineering Press, Bellingham, Washington, USA, 1993
6. A. Natarajan C. K. Tsai S. I. Khan P. McCarren K. N. Houk M. A. Garcia-Garibay The, photoarrangement of α-santonin is a single-crystal-to-single-crystal reaction: a long kept secret in solid-state organic chemistry revealed J. Am. Chem. Soc. 2007 129 9846
7. Synthesis organica by means of light, ed., M. D'Auria, Societa Chimica Italiana, Roma, 2009
8. B. Shah D. C. Neckers The, photochemistry of benzophenone The Spectrum 2003 16 18
9. E. Paternò Sintesi, in chimica organica per mezzo della luce - Nota I Introduzione Gazz. Chim. Ital. 1909 39 237
10. M. Olivucci, Ed. Computational Photochemistry, Elsevier, Amsterdam, 2005
11. A. Kutateladze, Ed, Computational methods photochemistry, Taylor and Francis, Boca Raton, 2005
12. N. J. Turro, V. Ramamurthy, J. C. Scaiano Principles, of Molecular Photochemistry. An Introduction, University Science Books, Sausalito, CA, 2009
13. R. A. Dushl Restructuring, Science Education. The Importance of Theories and their Development Teachers College, Columbia University: New York, 1990
14. P. Klan, J. Wirz, Photochemistry, of Organic Compounds. From Concepts to Practice, Wiley, West Sussex, 2009
15. L. O. Bjorn, Ed, Photobiology. The Science of Life and Light, Springer Science, New York, 2008
16. L. Pauling Nature of forces between large molecules of biological interest Nature 1948 161 707
17. A. Radzicka R. Wolfenden A proficient enzyme Science 1995 267 90
18. L.-O. Essen Photolyases, and cryptochromes: common mechanisms of DNA repair and light-driven signaling? Curr. Opin. Struct. Biol. 2006 16 51
19. S. T. Kims P. F. Heelis A. Sancar Biochemistry 1992 31 11244
20. A. Mess T. Lar U. Hannecke A. P. M. Eker T. Carell L. O. Essen Crystal, structure of a photolyase bound to a cpd-like dna lesion after in situ repair Science 2004 306 1789
21. Xiyun Zhang K. N. Houk Why enzymes are proficient catalysts: beyond the pauling paradigm Acc. Chem. Res. 2005 38 379
22. C. E. Shannon, W. Weaver, The Mathematical Theory of Communication, Urbana-Champaigne, IL, Illini Books, 1963
23. http://bayes.wustl.edu/etj/etj.html (accessed November 2, 2010)
24. D. Bonchev., in Complexity in Chemistry. Introduction and Fundamentals, ed., D Bonchev, and, D. H. Rouvray, Taylor and Francis, London, 2003, Ch. 4
25. M. A. Garcia-Garibay Chemical reactivity in organized media: statistical entropy and information in crystals and enzymes Curr. Opin. Solid State Mater. Sci. 1988 3/4 399
26. Y. Tapuhi O. Kalisky I. Agranat J. Org. Chem. 1979 44 1949
27. J. I Seeman Effect of conformational change on reactivity in organic chemistry. Evaluations, applications, and extensions of Curtin-Hammett Winstein-Holness kinetics Chem. Rev. 1983 83 83
28. H. E. Zimmerman G. L. Grunewald The, chemistry of barrelene. iii. a unique photoisomerization to semibullvalene J. Am. Chem. Soc. 1966 88 183
29. L. M. Frutos U. Sancho O. Castaño Triplet versus singlet photoreaction mechanism in the barrelene di-π-methane rearrangement Org. Lett. 2004 6 1229
30. N. J. Turro B. Kraeutler Magnetic, field and magnetic isotope effects in organic photochemical reactions. A novel probe of reaction mechanisms and a method for enrichment of magnetic isotopes Acc. Chem. Res. 1980 13 369
31. N. J. Turro A. L. Buchachenko V. F. Tarasov How, spin stereochemistry severely complicates the formation of a carbon-carbon bond between two reactive radicals in a supercage Acc. Chem. Res. 1995 28 69
32. C. T. Rodgers P. J. Hore Chemical, magnetoreception in birds: The radical pair mechanism Proc. Natl. Acad. Sci. U. S. A. 2009 106 353
33. S. Schlundt G. Kuzmanich F. Spaning G. de Miguel Rojas C. Kovacs M. A. Garcia-Garibay D. M. Guldi A. Hisrch Dendritic Porphyrin-fullerene conjugates -efficient lightharvesting and charge transfer events Chem.-Eur. J. 2009 15 12223
34. C. Müller A. Bauer T. Bach Light-driven, enantioselective organocatalysis Angew. Chem., Int. Ed. 2009 48 6640
35. M. A. Garcia-Garibay Engineering carbene rearrangements in crystals: from molecular information to solid-state reactivity Acc. Chem. Res. 2003 36 491
36. S. Shin A. E. Keating D. Cizmeciyan S. I. Khan M. A. Garcia-Garibay Control, of carbene reactivity by crystals. a highly selective 1,2-h shift in the solid-to-solid reaction of 1-(4′-biphenyl)-2-phenyldiazopropane to; (z)-1-(4′-biphenylyl)-2-phenylpropene J. Am. Chem. Soc. 1997 119 1859
37. J. Anastas, W. Warner Green Chemistry, Theory and Practice, Oxford University Press, Oxford, 1998
38. C. J. Mortko M. A. Garcia-Garibay Stereospecific, synthesis of compounds with adjacent chiral quaternary centers in solid-to-solid reactions Top. Stereochem. 2006 25 205
39. N. V. Lebedeva V. F. Tarasov M. J. E. Resendiz M. A. Garcia-Garibay R. C. White Forbes, M. D. E. The, missing link between molecular triplets and spin-polarized free radicals: room temperature triplet states of nanocrystalline radical pairs J. Am. Chem. Soc. 2010 132 82
40. M. E. Ellison D. Ng H. Dang M. A. Garcia-Garibay Enantiospecific, synthesis of vicinal stereogenic tertiary and quaternary centers by combination of configurationally trapped radical pairs in crystalline solids Org. Lett. 2003 5 2531
41. D. Ng Z. Yang M. A. Garcia-Garibay Total, synthesis of (±)-herbertenolide by stereospecific formation of vicinal quaternary centers in a crystalline ketone Org. Lett. 2004 6 645 647
42. A. Natarajan D. Ng Z. Yang M. A. Garcia-Garibay A green chemistry method for the synthesis of compounds with adjacent quaternary stereogenic centers: parallel syntheses of (+) and (-)-a-cuparenone by radical combination in crystalline solids Angew. Chem., Int. Ed. 2007 46 6485 6487
43. P. F. Fox, and P. L. H. McSweeney, Dairy Chemistry and Biochemistry, Chapman & Hall, London, 1998
44. H. Kasai H. S. Nalwa H. Oikawa S. Okada H. Matsuda N. Minami A. Kakuta K. Ono A. Mukoh H. Nakanishi Jpn. J. Appl. Phys. 1992 31 L1132
45. M. Veerman M. J. E. Resendiz M. A. Garcia-Garibay Large-scale, photochemical reactions of nanocrystalline suspensions: a promising green chemistry method Org. Lett. 2006 8 2615 17
46. K. K. Chin A. Natarajan L. M. Campos E. Johansson H. Shepherd M. A. Garcia-Garibay Pump-probe, spectroscopy and circular dichroism of nanocrystalline benzophenone - towards absolute kinetic measurements in solid state photochemical reactions Chem. Commun. 2007 4266
47. M. J. E. Resendiz J. Taing M. A. Garcia-Garibay Photodecarbonylation, of 1,3-dithiophenyl propanone: using nanocrystals to overcome the filtering effect of highly absorbing trace impurities Org. Lett. 2007 9 4351
48. G. Kuzmanich A. Natarajan K. K. Chin M. Veerman C. J. Mortko M. A. Garcia-Garibay Photonic, amplification by a singlet-state quantum chain photodecarbonylation reaction in crystalline diarylcyclopropenones J. Am. Chem. Soc. 2008 130 1140
49. G. Kuzmanich M. N. Gard Miguel A. Garcia-Garibay Photonic amplification by a singlet-state quantum chain photodecarbonylation reaction in crystalline diarylcyclopropenones J. Am. Chem. Soc. 2009 131 11606
50. R. C Powel A. G. Soos Singlet, exciton energy transfer in organic solids J. Lumin. 1975 11 1
51. S. Takeuchi T. Tahara Femtosecond, absorption study of photodissociation of diphenylcyclopropenone in solution: Reaction dynamics and coherent nuclear motion J. Chem. Phys. 2004 120 4768