Cation to anion triplet-triplet energy transfer in crystalline organic salts

Tetrahedron Letters

Volumn 37, Issue 34, 1996, Pages 6037-6040

  Gamlin, Janet N ^a   Olovsson, Gunnar ^a   Pitchumani, Kasi ^b   Ramamurthy, V ^b   Scheffer, John R ^a   Trotter, James ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 DIMETHYLAMINOPROPIOPHENONE; 4 ACETYLPYRIDINE; 4' PIPERAZINOACETOPHENONE; CARBOXYLIC ACID; PHOTOSENSITIZING AGENT; PROPIOPHENONE DERIVATIVE; UNCLASSIFIED DRUG;

ANION EXCHANGE; ARTICLE; CATION EXCHANGE; CHEMICAL REACTION KINETICS; CRYSTAL STRUCTURE; ENERGY TRANSFER; PHOTOCHEMISTRY; PHOTOSENSITIVITY; SPECTRAL SENSITIVITY; STRUCTURE ACTIVITY RELATION;

EID: 0030593601     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01309-3     Document Type: Article

References (11)

1. 1. Gamlin, J.N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J.R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203.
2. 2. See, however, Garcia-Garibay, M.; Scheffer, J.R.; Trotter, J.; Wireko, F. Tetrahedron Lett. 1987, 28, 1741.
3. 3. (a) Such singlet-triplet reactivity differences are characteristic of ethenoanthracenes that do not possess carbonyl-containing substituents attached to the bridging double bond. See Scheffer, J.R.; Yang, J. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W.M.; Song, P-S., Eds.; CRC Press: Boca Raton, FL, 1995, Chapter 16;
4. (b) For a recent, general review of the di-π-methane photorearrangement, see Zimmerman, H.E. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1991, vol. 11, Chapter 1.
5. 4. Chen, J.; Scheffer, J.R.; Trotter, J. Tetrahedron 1992, 48, 3251.
6. 5. Cristol, S.J.; Noreen, A.L. J. Org. Chem. 1976, 41, 4016;
7. (b) Cristol, S.J.; Schloemer, G.C.; James, D.R.; Paquette, L.A. J. Org. Chem. 1972, 37, 3852.
8. 3a
9. 7. Salt 1·5: C2/c; a = 37.712(3), b = 8.977(1), c = 15.922(1) Å; β = 92.055(6)°; Z = 8; R = 4.5%. Complex 1·6: P1; a = 12.344(1), b = 18.439(3), c = 8.2721(7) Å; α = 101.789(9), β = 94.525(8), γ = 95.05(1)°; Z = 2; R = 5.1%. Salt 1·7: P1; a = 9.760(1), b = 16.254(2), c = 9.114(1) Å; α = 99.47(1), β = 109.17(1), γ = 88.10(1)°; Z = 2; R = 4.4%. Full crystallographic details will be published separately.
10. 8. A negative feature of the high molar extinction coefficient of salt 1·7 is a very shallow photon penetration depth within the crystal. For this reason, it is important that finely crushed samples be used.
11. 9. Whether the double bond is more relevant for energy transfer than one of the benzo rings of substrate 1 is a moot point. For adducts in which the bridging double bond bears conjugating substituents, this site is certainly implicated as the locus of initial excitation.