The meso-β-linkage as structural motif in porphyrin-based donor-acceptor compounds

Tetrahedron Letters

Volumn 45, Issue 17, 2004, Pages 3363-3367

  Senge, Mathias O ^a   Rößler, Beatrice ^b   Von Gersdorff, Jörg ^b   Schäfer, Andreas ^b   Kurreck, Harry ^b  

^a UNIVERSITY OF POTSDAM   (Germany)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Condensation reactions; Electron transfer; Porphyrin quinones, porphyrins; Tetrapyrroles

Indexed keywords

1,4 BENZOQUINONE; ALDEHYDE DERIVATIVE; FUNCTIONAL GROUP; METHANE; PORPHYRIN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; ISOMER; SYNTHESIS; X RAY ANALYSIS;

EID: 1842731111     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.027     Document Type: Article

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27. max (rel. ε ) = 419 (1.0), 455 (0.77), 520 (0.17), 591 (0.08), 672 nm (0.057).
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32. max=0.839, solvate molecules disordered. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC-230767. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ).
33. 2 followed by column chromatography on silica gel eluting with n-hexane/acetic acid ester (3.5:1, v/v). The main fraction was subjected to preparative HPLC (silica 5μ, diisopropyl ether/n-hexane = 3:7) yielding 12 (15 mg, 9%) and 14 (10 mg, 6%). Although many other products can be formed under the reaction conditions, the target compounds are easily identified as they are red and nonfluorescent on TLC.
34. max (rel. ε ) = 252 (0.16), 421 (1.0), 443 (0.96), 522 (0.14), 559 (0.07), 597 (0.055), 658 nm (0.055).
35. max (rel. ε ) = 15: 422 (1.0), 444 (0.95), 557 (0.12), 603 (0.036), ∼635; 16: 422 (0.98), 442 (1.0), 535 (sh), 552 (0.1), 610 (sh), 666 (0.028); 17: 421 (1.0), 440 (0.91), 518 (0.11), 559 (0.09), 602 (0.06), 635 nm (0.015).