Abstract
The electronic spectra and structures of sterically hindered molecules of unsymmetrical ortho-analogs of POPOP containing electron donor subsitituents in the oxadiazole part of the molecule have been studied (1-(5′-phenyloxazol-2-yl)-2-(5-phenyl-1,3,4-oxadiazol-2-yl)benzene derivatives (I)). X-Ray structural analysis was carried out on the dimethylamino derivative of I. It was found that the conformation of the molecules of the investigated compounds is determined by the conformation of the starting 2-(5-phenyloxazol-2-yl)benzoic acid and its acid chloride used in the synthesis of the ortho POPOP analogs. In the series of unsymmetrical ortho POPOP analogs there arises a unique possibility for changes in the structure of the oxadiazole part of the molecule to affect the position of the spectral emission almost without affecting the long wavelength absorption band in the process. There were thus prepared efficient organic luminophores having an anomalously large Stokes fluorescence shift.
Similar content being viewed by others
References
F. Vollmer, W. Rettig, and E. Birkner, J. Fluoresc.,4, 65 (1994).
A. O. Doroshenko, L. D. Patsenker, V. N. Baumer, L. V. Chepeleva, A. V. Vankevich, O. P. Shilo, S. N. Yarmolenko, V. M. Shershukov, V. G. Mitina, and O. A. Ponomarev, Zh. Obshch. Khim.,64, 646 (1994).
A. O. Doroshenko, L. D. Patsenker, V. N. Baumer, L. V. Chepeleva, V. N. Van'kevich, A. V. Kirichenko, S. N. Yarmolenko, V. M. Scherschukov, V. G. Mitina, and O. A. Ponomaryov Mol. Eng.3, 353 (1994).
A. O. Doroshenko, A. V. Kirichenko, V. G. Mitina, and O. A. Ponomaryov, J. Photochem. Photobiol.,94, 15 (1996).
M. J. S. Dewar, E. G. Zoebich, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc.,107, 3902 (1985).
V. N. Baumer, A. O. Doroshenko, A. A. Verezubova, L. M. Ptyagina, A. V. Kirichenko, and O. A. Ponomarev, Khim. Geterotsikl. Soedin., No. 7, 984 (1996).
W. A. Melhuish, J. Phys. Chem.,65, 229 (1961).
G. M. Sheldrick, SHELXTL PLUS. A System of Computer Programs for the Determination of Crystal Structure from X-Ray Diffraction Data, Siemens Analytical X-Ray Instruments Co. (1990).
Additional information
Kharkov State University, Kharkov 310077. Institutefor Monocrystals. National Academy of Sciences of Ukraine, Kharkov 310001. Translated from Khimiya Geterotsiklicheskikh Soedinenii. No. 11, pp. 1549–1558, November, 1997.
Rights and permissions
About this article
Cite this article
Doroshenko, A.O., Baumer, V.N., Kirichenko, A.V. et al. Molecular structural features of unsymmetrical ortho analogs of POPOP. Chem Heterocycl Compd 33, 1341–1349 (1997). https://doi.org/10.1007/BF02320339
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02320339