Conformational change from a twisted figure-eight to an open-extended structure in doubly fused 36π core-modified octaphyrins triggered by protonation: Implication on photodynamics and aromaticity

Chemistry - A European Journal

Volumn 19, Issue 50, 2013, Pages 17011-17020

  Karthik, Ganesan ^a   Lim, Jong Min ^b   Srinivasan, A ^a   Suresh, C H ^c   Kim, Dongho ^b   Chandrashekar, Tavarekere K ^a  

^a INSTITUTE OF PHYSICS   (India)

^b Yonsei University   (South Korea)

^c REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

aromaticity; conformation analysis; fused ring systems; photodynamics; X ray diffraction

Indexed keywords

ABSORPTION SPECTROSCOPY; AROMATIC COMPOUNDS; AROMATIZATION; CHEMICAL SHIFT; CONFORMATIONS; ELECTRONIC STRUCTURE; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTONS; PROTONATION; SINGLE CRYSTALS; TWO PHOTON PROCESSES; X RAY DIFFRACTION;

2 ,3-DICHLORO-5 ,6-DICYANO-1 ,4-BENZOQUINONE; AROMATICITIES; CONFORMATION ANALYSIS; FUSED-RING SYSTEM; NUCLEUS INDEPENDENT CHEMICAL SHIFTS; PHOTODYNAMICS; SINGLE CRYSTAL X-RAY STRUCTURES; TWO-PHOTON ABSORPTION CROSS SECTION;

CRYSTAL ATOMIC STRUCTURE;

BENZOQUINONE DERIVATIVE; DICHLORODICYANOBENZOQUINONE; PORPHYRIN; THIOPHENE DERIVATIVE;

AROMATICITY; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CONFORMATION ANALYSIS; ELECTRON; FUSED-RING SYSTEMS; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; PHOTODYNAMICS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

AROMATICITY; CONFORMATION ANALYSIS; FUSED-RING SYSTEMS; PHOTODYNAMICS; X-RAY DIFFRACTION;

BENZOQUINONES; CRYSTALLOGRAPHY, X-RAY; ELECTRONS; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; PORPHYRINS; THIOPHENES;

EID: 84889582009     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201302020     Document Type: Article

References (67)

1. M. O. Senge, M. Fazekas, E. G. A. Notaras, W. J. Blau, M. Zawadzka, O. B. Locos, M. N. Mhuircheartaigh, Adv. Mater. 2007, 19, 2737-2774
2. J. Y. Shin, K. S. Kim, M. C. Yoon, J. M. Lim, Z. S. Yoon, A. Osuka, D. Kim, Chem. Soc. Rev. 2010, 39, 2751-2767
3. J. M. Lim, Z. S. Yoon, J. Y. Shin, K. S. Kim, M. C. Yoon, D. Kim, Chem. Commun. 2009, 261-273
4. T. K. Chandrashekar, S. Venkatraman, Acc. Chem. Res. 2003, 36, 676-696
5. R. Misra, R. Kumar, T. K. Chandrashekar, C. H. Suresh, A. Nag, D. Goswami, J. Am. Chem. Soc. 2006, 128, 16083-16091
6. H. Rath, J. Sankar, V. Prabhuraja, T. K. Chandrashekar, A. Nag, D. Goswami, J. Am. Chem. Soc. 2005, 127, 11608-11609.
7. R. Bonnett, Chem. Soc. Rev. 1995, 24, 19-33
8. J. L. Sessler, S. J. Weghorn, Expanded, Contracted and Isomeric Porphyrins, Pergamon, New York, 1997, 15, 429-503
9. C. R. Karunakaran, P. S. S. Babu, M. B. Betsy, K. P. Albish, A. S. Nair, K. S. Rao, A. Srinivasan, T. K. Chandrashekar, C. M. Rao, R. Pillai, D. Ramaiah, ACS Chem. Biol. 2013, 8, 127-132.
10. A. Jasat, D. Dolphin, Chem. Rev. 1997, 97, 2267-2340
11. A. Srinivasan, M. V. R. Reddy, S. J. Narayanan, B. Sridevi, K. S. Pushpan, M. Ravikumar, T. K. Chandrashekar, Angew. Chem. 1997, 109, 2710-2713
12. Angew. Chem. Int. Ed. Engl. 1997, 36, 2598-2601
13. B. Sridevi, S. J. Narayanan, R. Rao, T. K. Chandrashekar, U. Englich, K. R. Senge, Inorg. Chem. 2000, 39, 3669-3677.
14. M. B. Winter, P. J. Klemm, C. M. Phillips-Piro, K. N. Raymond, M. A. Marletta, Inorg. Chem. 2013, 52, 2277-2279.
15. Z. S. Yoon, A. Osuka, D. Kim, Nat. Chem. 2009, 1, 113-122
16. J. Wu, I. Fernandez, P. v. R. Schleyer, J. Am. Chem. Soc. 2013, 135, 315-321.
17. R. Misra, T. K. Chandrashekar, Acc. Chem. Res. 2008, 41, 265-279
18. Y. Pareek, M. Ravikanth, T. K. Chandrashekar, Acc. Chem. Res. 2012, 45, 1801-1816.
19. M. Stȩpień, N. Sprutta, L. Latos-Grażyński, Angew. Chem. 2011, 123, 4376-4430
20. Angew. Chem. Int. Ed. 2011, 50, 4288-4340
21. S. Saito, A. Osuka, Angew. Chem. 2011, 123, 4432-4464
22. Angew. Chem. Int. Ed. 2011, 50, 4342-4373.
23. P. J. Chmielewski, L. Latos-Grażyński, K. Rachlewicz, Chem. Eur. J. 1995, 1, 68-72
24. N. Sprutta, L. Latos-Grażyński, Org. Lett. 2001, 3, 1933-1935
25. S. Shimizu, R. Taniguchi, A. Osuka, Angew. Chem. 2005, 117, 2265-2269
26. Angew. Chem. Int. Ed. 2005, 44, 2225-2229.
27. H. Furuta, T. Ishizuka, A. Osuka, T. Ogawa, J. Am. Chem. Soc. 1999, 121, 2945-2946
28. T. K. Chandrashekar, V. Prabhuraja, S. Gokulnath, R. Sabarinathan, A. Srinivasan, Chem. Commun. 2010, 46, 5915-5917.
29. H. Furuta, T. Asano, T. Ogawa, J. Am. Chem. Soc. 1994, 116, 767-768
30. P. J. Chmielewski, L. Latos-Grażyński, K. Rachlewicz, T. Glowiak, Angew. Chem. 1994, 106, 805-808
31. Angew. Chem. Int. Ed. Engl. 1994, 33, 779-781.
32. E. Vogel, M. Bröring, J. Fink, D. Rosen, H. Schmickler, J. Lex, K. W. K. Chan, Y.-D. Wu, D. A. Plattner, M. Nendel, K. N. Houk, Angew. Chem. 1995, 107, 2705-2709
33. Angew. Chem. Int. Ed. Engl. 1995, 34, 2511-2514.
34. A. Osuka, S. Saito, Chem. Commun. 2011, 47, 4330-4339
35. E. Pacholska-Dudziak, J. Skonieczny, M. Pawlicki, L. Szterenberg, Z. Ciunik, L. Latos-Grażyński, J. Am. Chem. Soc. 2008, 130, 6182-6195.
36. G. Karthik, M. Sneha, V. Prabhuraja, J. M. Lim, D. Kim, A. Srinivasan, T. K. Chandrashekar, Chem. Eur. J. 2013, 19, 1886-1890
37. V. G. Anand, S. Saito, S. Shimizu, A. Osuka, Angew. Chem. 2005, 117, 7410-7414
38. Angew. Chem. Int. Ed. 2005, 44, 7244-7248
39. M. Suzuki, A. Osuka, J. Am. Chem. Soc. 2007, 129, 464-465.
40. S. Saito, J. Y. Shin, J. M. Lim, K. S. Kim, D. Kim, A. Osuka, Angew. Chem. 2008, 120, 9803-9806
41. Angew. Chem. Int. Ed. 2008, 47, 9657-9660.
42. M. Alonso, P. Geerlings, F. D. Proft, Chem. Eur. J. 2013, 19, 1617-1622.
43. S. Mori, A. Osuka, J. Am. Chem. Soc. 2005, 127, 8030-8032
44. Y. Tanaka, S. Saito, S. Mori, N. Aratani, H. Shinokubo, N. Shibata, Y. Higuchi, Z. S. Yoon, K. S. Kim, S. B. Noh, J. K. Park, D. Kim, A. Osuka, Angew. Chem. 2008, 120, 693-696
45. Angew. Chem. Int. Ed. 2008, 47, 681-684.
46. M. Stȩpień, L. Latos-Grażyński, N. Sprutta, P. Chwalisz, L. Szterenberg, Angew. Chem. 2007, 119, 8015-8019
47. Angew. Chem. Int. Ed. 2007, 46, 7869-7873.
48. J. Sankar, S. Mori, S. Saito, H. Rath, M. Suzuki, Y. Inokuma, H. Shinokubo, K. S. Kim, Z. S. Yoon, J. Y. Shin, J. M. Lim, Y. Matsuzaki, O. Matsushita, A. Muranaka, N. Kobayashi, D. Kim, A. Osuka, J. Am. Chem. Soc. 2008, 130, 13568-13579.
49. J. K. Park, Z. S. Yoon, M. C. Yoon, K. S. Kim, S. Mori, J. Y. Shin, A. Osuka, A. D. Kim, J. Am. Chem. Soc. 2008, 130, 1824-1825.
50. J. M. Lim, J. Y. Shin, Y. Tanaka, S. Saito, A. Osuka, D. Kim, J. Am. Chem. Soc. 2010, 132, 3105-3114.
51. O. K. Kim, K. S. Lee, H. Y. Woo, K. S. Kim, G. S. He, J. Swiatkiewicz, P. N. Prasad, Chem. Mater. 2000, 12, 284-290
52. J. Frey, A. D. Bond, A. B. Holmes, Chem. Commun. 2002, 2424-2425
53. I. Palamà, F. D. Maria, I. Viola, E. Fabiano, G. Gigli, C. Bettini, G. Barbarella, J. Am. Chem. Soc. 2011, 133, 17777-17785.
54. Z. Zhang, J. M. Lim, M. Ishida, V. Roznyatovskiy, V. Lynch, H. Y. Gong, X. Yang, D. Kim, J. L. Sessler, J. Am. Chem. Soc. 2012, 134, 4076-4079.
55. M. Gouterman, J. Mol. Spectrosc. 1961, 6, 138-163.
56. A. D. J. Becke, J. Chem. Phys. 1993, 98, 1372-1377
57. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-790.
58. T. M. Krygowski, J. Chem. Inf. Comput. Sci. 1993, 33, 70-78
59. T. M. Krygowski, M. K. Cyranski, Chem. Rev. 2001, 101, 1385-1390.
60. J. Kruszewski, T. M. Krygowski, Tetrahedron Lett. 1972, 13, 3839-3842
61. P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. E. Hommes, J. Am. Chem. Soc. 1996, 118, 6317-6318.
62. D. Geuenich, K. Hess, F. Kohler, R. Herges, Chem. Rev. 2005, 105, 3758-3772
63. E. Steiner, P. W. Fowler, Org. Biomol. Chem. 2006, 4, 2473-2476.
64. R. Berera, R. v. Grondelle, J. T. M. Kennis, Photosynth. Res. 2009, 101, 105-118.
65. M. C. Yoon, R. Misra, Z. S. Yoon, K. S. Kim, J. M. Lim, T. K. Chandrashekar, D. Kim, J. Phys. Chem. B 2008, 112, 6900-6909.
66. J. Y. Shin, J. M. Lim, Z. S. Yoon, K. S. Kim, M. C. Yoon, S. Hiroto, H. Shinokubo, S. Shimizu, A. Osuka, D. Kim, J. Phys. Chem. B 2009, 113, 5794-5802.
67. E. Heilbronner, Tetrahedron Lett. 1964, 5, 1923-1928.