Collect. Czech. Chem. Commun.
2009, 74, 131-146
https://doi.org/10.1135/cccc2008154
Published online 2009-01-29 18:06:27
Experimental and computed dipole moments in donor–bridge–acceptor systems with p-phenylene and p-carboranediyl bridges
Ladislav Droža, Mark A. Foxb, Drahomír Hnykc,*, Paul J. Lowb, J. A. Hugh MacBrideb and Václav Všetečkaa
a Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030, CZ-128 40 Prague 2, Czech Republic
b Department of Chemistry, University of Durham, South Road, Durham, DH1 3LE, UK
c Institute of Inorganic Chemistry, Academy of Sciences of the Czech Republic, v.v.i., No. 1001, CZ-250 68 Husinec-Řež, Czech Republic
References
1a. Prasad P. N., Williams D. J.: Nonlinear Optical Effects in Molecules and Polymers. Wiley, New York 1991.
1b. Chemla D. S., Zyss J.: Nonlinear Optical Properties of Organic Molecules and Crystals. Academic Press, New York 1987.
2. Chem. Phys. Lett. 1974, 29, 277.
< A., Ratner M. A.: https://doi.org/10.1016/0009-2614(74)85031-1>
3. Exner O.: Dipole Moments in Organic Chemistry. Georg Thieme Publishers, Stuttgart 1975.
4. J. Mol. Struct. (THEOCHEM) 2007, 803, 9.
< S., Exner O.: https://doi.org/10.1016/j.theochem.2006.09.008>
5a. Inorg. Chem. 1998, 37, 3454.
< P. v. R., Najafian K.: https://doi.org/10.1021/ic980110v>
5b. Dalton Trans. 2006, 3544.
< M. A., Cameron A. M., Low P. J., Paterson M. A. J., Batsanov A. S., Goeta A. E., Rankin D. W. H., Robertson H. E., Schirlin J. T.: https://doi.org/10.1039/b517538k>
5c. Dalton Trans. 2005, 1310.
< A. R., Robertson H. E., Borisenko K. B., Rankin D. W. H., Fox M. A.: https://doi.org/10.1039/b418276f>
6. J. Chem. Soc., Dalton Trans. 1998, 401.
< M. A., MacBride J. A. H., Peace R. J., Wade K.: https://doi.org/10.1039/a707154j>
7a. Chem. Commun. 2001, 1610.
< M. A., Paterson M. A. J., Nervi C., Galeotti F., Puschmann H., Howard J. A. K., Low P. J.: https://doi.org/10.1039/b104307m>
7b. Tetrahedron Lett. 2001, 42, 6327.
< Y., Taoda Y.: https://doi.org/10.1016/S0040-4039(01)01250-3>
7c. Organometallics 2004, 23, 482.
< T. J., Herzog A., Huertas R., Lee M. W., Knobler C. B., Hawthorne M. F.: https://doi.org/10.1021/om030514h>
7d. C. R. Chim. 2005, 8, 1883.
< B., Costuas K., Halet J. F., Nervi C., Paterson M. A. J., Fox M. A., Roberts R. L., Albesa-Jové D., Puschmann H., Howard J. A. K., Low P. J.: https://doi.org/10.1016/j.crci.2005.03.016>
7e. Inorg. Chem. 2006, 45, 4331.
< M., Schwab P. F. H., Indelli M. T., Chiorboli C., Scandola F.: https://doi.org/10.1021/ic060327m>
7f. J. Am. Chem. Soc. 2008, 130, 3566.
< M. A., Roberts R. L., Baines T. E., Le Guennic B., Halet J.-F., Hartl F., Yufit D. S., Albesa-Jové D., Howard J. A. K., Low P. J.: https://doi.org/10.1021/ja0779755>
8. Drož L.: Ph.D. Thesis. Charles University, Prague 2006; and references therein.
9. J. Chem. Soc. 1960, 1547.
< P., Gray G. W., Lewis D.: https://doi.org/10.1039/jr9600001547>
10. J. Chem. Soc. 1960, 2699.
< P., Gray G. W., Lewis D.: https://doi.org/10.1039/jr9600002699>
11. Chem. Heterocycl. Comp. 1983, 29.
< B. M., Popova N. A., Yushko E. G., Golyanskii B. V., Tur I. N.: https://doi.org/10.1007/BF00512809>
12. Trans. Faraday Soc. 1949, 45, 714.
< E. A.: https://doi.org/10.1039/tf9494500714>
13. Trans. Faraday Soc. 1950, 46, 256.
J. W.:
14. Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Montgomery J.A., Jr., Vreven T., Kudin K. N., Burant J. C., Millam J. M., Iyengar S. S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G. A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J. E., Hratchian H. P., Gross J. P., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Ayala P. Y., Morokuma K., Voth G. A., Salvador P., Dannenberg J. J., Zakrzewski V. G., Dapprich S., Daniels A. D., Strain M. C., Farkas O., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Ortiz J. V., Cui Q., Baboul A. G., Clifford S., Cioslowski J., Stefanov B. B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R. L., Fox D. J., Keith T., Al-Laham M. A., Peng C. Y., Nanayakkara A., Challacombe M., Gill P. M. W., Johnson B., Chen W., Wong M. W., Gonzalez C., Pople J. A.: Gaussian 03, Revision C.02. Gaussian, Inc., Wallingford, CT 2004.
15a. J. Chem. Phys. 1993, 98, 5648.
< A. D.: https://doi.org/10.1063/1.464913>
15b. Phys. Rev. B 1988, 37, 785.
< C., Yang W., Parr R. G.: https://doi.org/10.1103/PhysRevB.37.785>
16a. J. Chem. Phys. 1991, 94, 6081.
< G. A., Al-Laham M. A.: https://doi.org/10.1063/1.460447>
16b. J. Chem. Phys. 1988, 89, 2193.
< G. A., Bennett A., Tensfeldt T. G., Al-Laham M. A., Shirley W. A., Mantzaris J.: https://doi.org/10.1063/1.455064>
17a. For X-ray data of related terphenyls, see Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1977, 33, 1773.
< J. L., Cailleau H., Yelon W. B.: https://doi.org/10.1107/S0567740877007043>
17b. Mol. Liq. Cryst. 1989, 6, 113.
W., Paulus H., Fan Z. X., Ibrahim I. H., Mokhles M.:
17c. J. Cryst. Mol. Struct. 1978, 8, 81.
< D. B., Carpenter R. E., de Vries A., Reed J. W., Brown G. H.: https://doi.org/10.1007/BF01371519>
18a. For X-ray data of related diaryl-p-carboranes, see Macromolecules 1998, 31, 1694.
< H. M., Herbertson P. L., Wade K., Baxter I., Williams D. J.: https://doi.org/10.1021/ma971186y>
18b. Spec. Publ. R. Soc. Chem. 2000, 253, 59.
H. M., Lewis D. F., Herbertson P. L., Wade K., Baxter I., Williams D. J.:
18c. Chem. Commun. 2007, 2178.
< S., Ellis D., Rosair G. M., Welch A. J.: https://doi.org/10.1039/b618556h>
18d. J. Organomet. Chem. 2000, 597, 157.
< A. S., Fox M. A., Howard J. A. K., Wade K.: https://doi.org/10.1016/S0022-328X(99)00672-5>
19. McClellan A. L.: Tables of Experimental Dipole Moments. W. H. Freeman & Co., San Francisco, London 1963.
20. Collect. Czech. Chem. Commun. 2001, 66, 1375.
< D., Všetečka V., Drož L., Exner O.: https://doi.org/10.1135/cccc20011375>
21a. Chem. Phys. 1991, 153, 457.
< M., Fort A., Klein G., Boeglin A., Serbutoviez C., Oswald L., Nicoud J. F.: https://doi.org/10.1016/0301-0104(91)80058-P>
21b. Chem. Phys. 1992, 164, 395.
< M., Fort A., Klein G., Serbutoviez C., Oswald L., Nicoud J. F.: https://doi.org/10.1016/0301-0104(92)87077-M>
22a. J. Mol. Struct. (THEOCHEM) 1993, 281, 21.
< A.-D., Pesquer M.: https://doi.org/10.1016/0166-1280(93)80024-T>
22b. J. Phys. Chem. 1996, 100, 9678.
< A. M., Wilbrandt R.: https://doi.org/10.1021/jp960013s>