Synthesis, crystal structure, and nonlinear optical behavior of β-unsubstituted meso-meso E-vinylene-linked porphyrin dimers

Organic Letters

Volumn 7, Issue 24, 2005, Pages 5365-5368

  Frampton, Michael J ^a   Akdas, Huriye ^a   Cowley, Andrew R ^a   Rogers, Joy E ^b   Slagle, Jonathan E ^b   Fleitz, Paul A ^b   Drobizhev, Mikhail ^c   Rebane, Aleksander ^c   Anderson, Harry L ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b AIR FORCE RESEARCH LABORATORY   (United States)

^c MONTANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28844499380     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0520525     Document Type: Article

References (37)

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18. Several related structures of β-alkyl meso-vinylene-linked porphyrinchlorin dimers and bischlorins have been reported, as well as a bispyropheophorabide-a: (a) Jaquinod, L.; Nurco, D. J.; Medforth, C. J.; Pandey, R. K.; Forsyth, T. P.; Olmstead, M. M.; Smith, K. M. Angew. Chem., Int. Ed. 1996, 35, 1013.
19. 2 bischlorin, and 79° in the free-base bispyropheophorabide-a. The presence of a saturated tetrahedral center at the β-position adjacent to the E-vinylene bridge reduces the steric interaction of a β-ethyl substituent at this position with the E-vinylene bridge and favors a more conjugated conformation.
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22. 22b (with Ph rather than Ar substituents), by a route similar to Scheme 1', has been reported in a patent: (a) Therien, M. J.; DiMagno, S. G. U.S. Patent 5,371,199, 1994.
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31. 2 requires 1901.0).
32. w = 0.0878 for all 16 237 unique reflections. The data have been deposited with the Cambridge Crystallographic Data Center, CCDC No. 276947.
33. F = 0.11; Seybold, P. G.; Gouterman, M. J. Mol. Spectrosc. 1969, 31, 1.
34. 22a is red-shifted by 77 nm, relative to the corresponding porphyrin monomer, and its electrochemical gap is reduced by 0.34 V.
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