Use of linker for preparation of missing solid-state photoproducts: head-to-head photodimerization of anthracene-9-propionic acid in its crystalline double salt with cyclohexane-1,2-diamine

Abstract

In order to realize the uncommon head-to-head photodimerization of 9-substituted anthracenes rather than the common head-to-tail photodimerization, a regiochemical control of the reaction through use of supramolecular linkers has been attempted in the solid state. Thus, crystalline double salts are prepared from anthracene-9-propionic acid (9-AP) and 1,2-diamines such as ethylenediamine (en), racemic or optically active (R,R)- or (S,S)-trans-cyclohexane-1,2-diamine (t-chxn), and cis-cyclohexane-1,2-diamine (c-chxn), and these salts are irradiated in the solid state. The 1,2-diamine is used as a linker molecule to connect two molecules of 9-AP by formation of a double salt. Like the previously published head-to-head photodimerization of (E)-cinnamic acids, the head-to-head photodimer of 9-AP is successfully produced from solid-state photolysis of the double salts of gauche 1,2-diamines, i.e. (R,R)- and (S,S)-t-chxn and c-chxn. The crystal structure for the low-photoreactivity double salt with (±)-t-chxn has been successfully solved.

References

1. Y. Ito, B. Borecka, J. Trotter and J. R. Scheffer, Tetrahedron Lett., 1995, 36, 6083.
2. Y. Ito, B. Borecka, G. Olovsson, J. Trotter and J. R. Scheffer, Tetrahedron Lett., 1995, 36, 6087.
3. D. O. Cowan and R. L. Drisko, Elements of Organic Photochemistry, Plenum, New York, 1976, pp. 37–47. More recently, however, the head-to-head photodimerizations of 9-substituted anthracenes have become fairly common (see ref. 4).
4. F. C. De Schryver, L. Anand, G. Smets and J. Switten, Polym. Lett., 1971, 777; G. Kaup and E. Teufel, Chem. Ber., 1980, 113, 3669; H. Bouas-Laurent, A. Castellan and J.-P. Desvergne, Pure Appl. Chem., 1980, 52, 2633; J.-P. Desvergne, A. Castellan and H. Bouas-Laurent, Tetrahedron Lett., 1981, 22, 3529; T. Wolff, J. Photochem., 1981, 16, 343; H.-D. Becker and V. Langer, J. Org. Chem., 1993, 58, 4703.
5. Y. Ito, Mol. Cryst. Liq. Cryst., 1996, 277, 247.
6. E. Heller and G. M. J. Schmidt, Isr. J. Chem., 1971, 9, 449.
7. M. D. Cohen, Z. Ludmer and V. Yakhot, Phys. Status Solidi B, 1975, 67, 51.
8. T. Wolff and N. Müller, J. Photochem., 1983, 23, 131.
9. M. D. Morse and J. P. Chesick, Acta Chrystallogr., Ser. B, 1976, 32, 954.
10. R. Horiguchi, N. Iwasaki and Y. Maruyama, J. Phys. Chem., 1987, 91, 5135; N. N. Barashkov, T. V. Sakhno, R. N. Nurmukhametov and O. A. Khakhel, Russ. Chem. Rev., 1993, 62, 539.
11. Z. Ludmer, Chem. Phys., 1977, 26, 113; G. E. Berkovic and Z. Ludmer, J. Am. Chem. Soc., 1982, 104, 4280.
12. T. Tamaki and T. Kokubu, J. Inclusion Phenom., 1984, 2, 815; T. Tamaki, T. Kokubu and K. Ichimura, Tetrahedron, 1987, 43, 1485.
13. C. I. Simionescu, G. Onofrei and M. Grigoras, Makromol. Chem., 1987, 188, 505.
14. Y. Ito, Mol. Cryst. Liq. Cryst., 1992, 219, 29.
15. Y. Ito and H. Fujita, J. Org. Chem., 1996, 61, 5677.
16. A. Altomare, M. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori and M. Camalli, J. Appl. Crystallogr., 1994, 27, 435.
17. Molecular Structure Corporation, teXsan Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA, 1995.