Structural studies of sparsely substituted synthetic chlorins and phorbines establish benchmarks for changes in the ligand core and framework of chlorophyll macrocycles

Journal of Molecular Structure

Volumn 979, Issue 1-3, 2010, Pages 27-45

  Taniguchi, Masahiko ^a   Mass, Olga ^a   Boyle, Paul D ^a   Tang, Qun ^b   Diers, James R ^b   Bocian, David F ^b   Holten, Dewey ^c   Lindsey, Jonathan S ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c WASHINGTON UNIVERSITY   (United States)

Author keywords

Aromaticity; Chiral volume; Chlorin; Chlorophyll; Isocyclic ring; Phorbine

Indexed keywords

AROMATICITIES; BOND ANGLE; BOND DISTANCE; CHIRAL VOLUME; CHLORINS; CORE CHANGES; CORE SIZE; DENSITY FUNCTIONALS; DERIVATIZATION OF; DFT CALCULATION; DIMETHYL GROUPS; FREE BASE; INDIVIDUAL FACTORS; MACROCYCLES; METAL COMPLEXATION; NATURALLY OCCURRING; PLANARITY; PORPHINE; RESONANCE RAMAN SPECTROSCOPY; STRETCHING VIBRATIONS; STRUCTURAL CHARACTERISTICS; STRUCTURAL STUDIES; SUPRAMOLECULAR ASSEMBLIES; TETRAPYRROLES; UNSYMMETRICAL STRUCTURE; X RAY DATA; X-RAY STUDIES;

CHLOROPHYLL; PORPHYRINS; RAMAN SPECTROSCOPY; STRETCHING; X RAYS;

X RAY CRYSTALLOGRAPHY;

EID: 77955427819     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2010.05.035     Document Type: Article

References (80)

1. M.O. Senge K.M. Kadish, K.M. Smith, R. Guilard, The Porphyrin Handbook vol. 10 2000 Academic Press San Diego, CA 1 218
2. W.R. Scheidt, and Y.J. Lee J.W. Buchler, Metal Complexes with Tetrapyrrole Ligands I, Structure and Bonding vol. 64 1987 Springer-Verlag Berlin, Germany 1 70
3. M. Ravikanth, and T.K. Chandrashekar J.W. Buchler, Coordination Chemistry Structure and Bonding vol. 82 1995 Springer-Verlag Berlin, Germany 105 188
4. B. Robert, R.J. Cogdell, and R. van Grondelle B.R. Green, W.W. Parson, Light-Harvesting Antennas in Photosynthesis 2003 Kluwer Academic Publishers The Netherlands 169 194
5. P. Fromme, E. Schlodder, and S. Jansson B.R. Green, W.W. Parson, Light-Harvesting Antennas in Photosynthesis 2003 Kluwer Academic Publishers The Netherlands 253 279
6. J. Gassmann, I. Strell, F. Brandl, M. Sturm, and W. Hoppe Tetrahedron Lett. 12 1971 4609
7. M.S. Fischer, D.H. Templeton, A. Zalkin, and M. Calvin J. Am. Chem. Soc. 94 1972 3613
8. K.M. Smith, D.A. Goff, J. Fajer, and K.M. Barkigia J. Am. Chem. Soc. 104 1982 3747
9. K.M. Smith, D.A. Goff, J. Fajer, and K.M. Barkigia J. Am. Chem. Soc. 105 1983 1674
10. K.M. Barkigia, L. Chantranupong, K.M. Smith, and J. Fajer J. Am. Chem. Soc. 110 1988 7566
11. M.O. Senge, F.W. Bobe, M.S. Huster, and K.M. Smith Liebigs Ann. Chem. 1991 871
12. M.O. Senge, and K.M. Smith Z. Kristallogr. 199 1992 239
13. L. Jaquinod, M.O. Senge, R.K. Pandey, T.P. Forsyth, and K.M. Smith Angew. Chem. Int. Ed. Engl. 35 1996 1840
14. S. Mettath, M. Shibata, J.L. Alderfer, M.O. Senge, K.M. Smith, R. Rein, T.J. Dougherty, and R.K. Pandey J. Org. Chem. 63 1998 1646
15. M.O. Senge, and K.M. Smith Acta Cryst. C53 1997 1314
16. C.F. Chee, N.A. Rahman, S.M. Zain, and S.W. Ng Acta Cryst. E64 2008 1986
17. O. Mass, M. Ptaszek, M. Taniguchi, J.R. Diers, H.-L. Kee, D.F. Bocian, D. Holten, and J.S. Lindsey J. Org. Chem. 74 2009 5276
18. C.E. Strouse Proc. Natl. Acad. Sci. USA 71 1973 325
19. H.-C. Chow, R. Serlin, and C.E. Strouse J. Am. Chem. Soc. 97 1975 7230
20. R. Serlin, H.-C. Chow, and C.E. Strouse J. Am. Chem. Soc. 97 1975 7237
21. C. Kratky, and J.D. Dunitz Acta Cryst. B31 1975 1586
22. C. Kratky, and J.D. Dunitz Acta Cryst. B33 1977 545
23. C. Kratky, H.P. Isenring, and J.D. Dunitz Acta Cryst. B33 1977 547
24. M.O. Senge, and K.M. Smith Photochem. Photobiol. 54 1991 841
25. M.O. Senge, and K.M. Smith Photochem. Photobiol. 60 1994 139
26. L. Jaquinod, D.J. Nurco, C.J. Medforth, R.K. Pandey, T.P. Forsyth, M.M. Olmstead, and K.M. Smith Angew. Chem. Int. Ed. Engl. 35 1996 1013
27. M.O. Senge, K. Ruhlandt-Senge, and K.M. Smith Z. Naturforsch. 50b 1995 139
28. S. Knapp, B. Huang, T.J. Emge, S. Sheng, K. Krogh-Jespersen, J.A. Potenza, and H.J. Schugar J. Am. Chem. Soc. 121 1999 7977
29. K.M. Barkigia, M.D. Berber, J. Fajer, C.J. Medforth, M.W. Renner, and K.M. Smith J. Am. Chem. Soc. 112 1990 8851
30. D.J. Nurco, C.J. Medforth, T.P. Forsyth, M.M. Olmstead, and K.M. Smith J. Am. Chem. Soc. 118 1996 10918
31. M.O. Senge, C.J. Medforth, T.P. Forsyth, D.A. Lee, M.A. Olmstead, W. Jentzen, R.K. Pandey, J.A. Shelnutt, and K.M. Smith Inorg. Chem. 36 1997 1149
32. K.M. Barkigia, D.J. Nurco, M.W. Renner, D. Melamed, K.M. Smith, and J. Fajer J. Phys. Chem. B 102 1998 322
33. M.O. Senge K.M. Kadish, K.M. Smith, R. Guilard, The Porphyrin Handbook vol. 1 2000 Academic Press San Diego, CA 239 347
34. J.A. Shelnutt, X.-Z. Song, J.-G. Ma, S.-L. Jia, W. Jentzen, and C.J. Medforth Chem. Soc. Rev. 27 1998 31
35. K. Kano, K. Fukuda, H. Wakami, R. Nishiyabu, and R.F. Pasternack J. Am. Chem. Soc. 122 2000 7494
36. P. Dastidar, and I. Goldberg Acta Cryst. C52 1996 1976
37. The term trapezoid is used here in the American definition to refer to a quadrilateral with two parallel sides. http://mathworld.wolfram.com/topics/ Quadrilaterals.html (accessed date 24.10.09).
38. M. Ptaszek, B.E. McDowell, M. Taniguchi, H.-J. Kim, and J.S. Lindsey Tetrahedron 63 2007 3826
39. M. Taniguchi, M. Ptaszek, B.E. McDowell, and J.S. Lindsey Tetrahedron 63 2007 3840
40. M. Taniguchi, M. Ptaszek, B.E. McDowell, P.D. Boyle, and J.S. Lindsey Tetrahedron 63 2007 3850
41. K.V. Berezin, and V.V. Nechaev Opt. Spectrosc. 97 2004 707
42. H.-L. Kee, C. Kirmaier, Q. Tang, J.R. Diers, C. Multhiah, M. Taniguchi, J.K. Laha, M. Ptaszek, J.S. Lindsey, D.F. Bocian, and D. Holten Photochem. Photobiol. 83 2007 1110
43. H.L. Kee, C. Kirmaier, Q. Tang, J.R. Diers, C. Muthiah, M. Taniguchi, J.K. Laha, M. Ptaszek, J.S. Lindsey, D.F. Bocian, and D. Holten Photochem. Photobiol. 83 2007 1125
44. J.S. Lindsey Acc. Chem. Res. 43 2010 300
45. D.K. Dogutan, M. Ptaszek, and J.S. Lindsey J. Org. Chem. 72 2007 5008
46. J.K. Laha, C. Muthiah, M. Taniguchi, and J.S. Lindsey J. Org. Chem. 71 2006 7049
47. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M.C. Burla, G. Polidori, and M. Camalli J. Appl. Cryst. 27 1994 435
48. Bruker-AXS, XL Version 6.12, Bruker-AXS, Madison, WI 53711, USA.
49. L.E. Webb, and E.B. Fleischer J. Chem. Phys. 43 1965 3100
50. B.M.L. Chen, and A. Tulinsky J. Am. Chem. Soc. 94 1972 4144
51. I. Saltsman, I. Goldberg, Y. Balasz, and Z. Gross Tetrahedron Lett. 48 2007 239
52. P.A. Connick, K.J. Haller, and K.A. Macor Inorg. Chem. 32 1993 3256
53. A.M. Stolzenberg, P.A. Glazer, and B.M. Foxman Inorg. Chem. 25 1986 983
54. M.O. Senge, K. Ruhlandt-Senge, and K.M. Smith Acta Cryst. C48 1992 1810
55. Except for molecular mechanics and semi-empirical models, the calculation methods used in Spartan have been documented in Y. Shao, L.F. Molnar, Y. Jung, J. Kussmann, C. Ochsenfeld, S.T. Brown, A.T.B. Gilbert, L.V. Slipchenko, S.V. Levchenko, D.P. O'Neill, R.A. DiStasio Jr., R.C. Lochan, T. Wang, G.J.O. Beran, N.A. Besley, J.M. Herbert, C.Y. Lin, T. Van Voorhis, S.H. Chien, A. Sodt, R.P. Steele, V.A. Rassolov, P.E. Maslen, P.P. Korambath, R.D. Adamson, B. Austin, J. Baker, E.F.C. Byrd, H. Dachsel, R.J. Doerksen, A. Dreuw, B.D. Dunietz, A.D. Dutoi, T.R. Furlani, S.R. Gwaltney, A. Heyden, S. Hirata, C.-P. Hsu, G. Kedziora, R.Z. Khalliulin, P. Klunzinger, A.M. Lee, M.S. Lee, W.Z. Liang, I. Lotan, N. Nair, B. Peters, E.I. Proynov, P.A. Pieniazek, Y.M. Rhee, J. Ritchie, E. Rosta, C.D. Sherrill, A.C. Simmonett, J.E. Subotnik, H.L. Woodcock III, W. Zhang, A.T. Bell, A.K. Chakraborty, D.M. Chipman, F.J. Keil, A. Warshel, W.J. Hehre, H.F. Schaefer III, J. Kong, A.I. Krylov, P.M.W. Gill, and M. Head-Gordon Phys. Chem. Chem. Phys. 8 2006 3172 3191
56. M.O. Senge, N.W. Smith, and K.M. Smith Inorg. Chem. 32 1993 1259
57. A. Pajunen, M.E. Stapelbroek-Möllmann, and P.H. Hynninen Acta Cryst. C52 1996 743
58. M.O. Senge, W.W. Kalisch, and S. Runge Tetrahedron 54 1998 3781
59. W.W. Kalisch, M.O. Senge, and K. Ruhlandt-Senge Photochem. Photobiol. 67 1998 312
60. M.O. Senge, M.G.H. Vicente, S.R. Parkin, H. Hope, and K.M. Smith Z. Naturforsch. 47b 1992 1189
61. R.J. Cogdell, T.D. Howard, N.W. Isaacs, K. McLuskey, and A.T. Gardiner Photosyn. Res. 74 2002 135
62. M.Z. Papiz, S.M. Prince, T. Howard, R.J. Cogdell, and N.W. Isaacs J. Mol. Biol. 326 2003 1523
63. D.E. Tronrud, M.F. Schmid, and B.W. Matthews J. Mol. Biol. 188 1986 443
64. V. Ermler, G. Fritzsch, S.K. Buchanan, and H. Michel Structure 2 1994 925
65. J. Deisenhofer, O. Epp, I. Sinning, and H. Michel J. Mol. Biol. 246 1995 429
66. M. Taniguchi, H.-J. Kim, D. Ra, J.K. Schwartz, C. Kirmaier, E. Hindin, J.R. Diers, S. Prathapan, D.F. Bocian, D. Holten, and J.S. Lindsey J. Org. Chem. 67 2002 7329
67. K.M. Barkigia, D.S. Gottfried, S.G. Boxer, and J. Fajer J. Am. Chem. Soc. 111 1989 6444
68. H. Scheer, and J.J. Katz K.M. Smith, Porphyrins and Metalloporphyrins 1975 Elsevier Scientific Publishing Company Amsterdam 501 503
69. J.L. Hoard K.M. Smith, Porphyrins and Metalloporphyrins 1975 Elsevier Scientific Publishing Company 340 341
70. J. Helaja, M. Stapelbroek-Möllmann, I. Kilpeläinen, and P.H. Hynninen J. Org. Chem. 65 2000 3700
71. S.M. Arabei, G.D. Egorova, K.N. Solov'ev, and S.F. Shkirman Zh. Prikl. Spektr. 40 1984 92 (English translation: J. Appl. Spectroscopy 40 (1984) 73)
72. F.H. Allen Acta Cryst. B58 2002 380
73. P.H. Hynninen, J. Helaja, F.-P. Montforts, and C.M. Müller J. Porphyr. Phthalocya. 8 2004 1376
74. G.A. Schick, and D.F. Bocian Biochim. Biophys. Acta 895 1987 127
75. A.N. Kozyrev, V. Suresh, S. Das, M.O. Senge, M. Shibata, T.J. Dougherty, and R.K. Pandey Tetrahedron 56 2000 3353
76. K.M. Barkigia, M.A. Thompson, J. Fajer, R.K. Pandey, K.M. Smith, and M.G.H. Vicente New J. Chem. 16 1992 599
77. K. Yamamoto, K. Sakata, N. Watanabe, A. Yagi, L.S. Brinen, and J. Clardy Tetrahedron Lett. 33 1992 2587
78. R.C. Pettersen J. Am. Chem. Soc. 93 1971 5629
79. A. Czader, and R.S. Czernuszewicz Org. Geochem. 38 2007 250
80. E. Prince (Ed.), International Tables for Crystallography, vol. C, third ed., Kluwer Academic Publishers, Inc., Dordrecht, The Netherlands, 2004, p. 700.