Abstract
A series of novel monomethylated salts derived from linear benzobisthiazole was prepared. The push-pull attributes of these new compounds are represented by a quaternised azolium cycle as the acceptor part at one end of the structure and the dialkylamino- or diarylamino-substituted benzene ring as the donor part at the opposite end. Both moieties are connected by a conjugated linker consisting of one or two double bonds. Such dipolar structures are promising candidates for non-linear optical materials. The quantum-chemical indices describing linear and non-linear optical properties were obtained from semi-empirical calculations. The relationships between the chemical structure and non-linear optical properties of the cations studied were obtained. Effective conjugation was confirmed by measuring the optical properties in the UV-VIS region.
[1] Armstrong, J. A., Bloembergen, N., Ducuing, J., & Pershan, P. S. (1962). Interactions between light waves in a nonlinear dielectric. Physical Reviews, 127, 1918–1939. DOI: 10.1103/PhysRev.127.1918. http://dx.doi.org/10.1103/PhysRev.127.191810.1103/PhysRev.127.1918Search in Google Scholar
[2] Balaganesan, B., Wen, S. W., & Chen, C. H. (2003). Synthetic study of tetramethyljulolidine—a key intermediate toward the synthesis of the red dopant DCJTB for OLED applications. Tetrahedron Letters, 44, 145–147. DOI: 10.1016/s0040-4039(02)02506-6. http://dx.doi.org/10.1016/S0040-4039(02)02506-610.1016/S0040-4039(02)02506-6Search in Google Scholar
[3] Becke, A. D. (1993). Density-functional thermochemistry. III. The role of exact exchange. The Journal of Chemical Physics, 98, 5648–5652. DOI: 10.1063/1.464913. 10.1063/1.464913Search in Google Scholar
[4] Finzi, C., & Grandolini, G. (1959). Research on benzobisthiazoles: linear benzothiazole. Gazzetta Chimica Italiana, 89, 2543–2554. Search in Google Scholar
[5] Fox, M. A. (1992). Electron transfer: A critical link between subdisciplines in chemistry. Chemical Reviews, 92, 365–368. DOI: 10.1021/cr00011a600. http://dx.doi.org/10.1021/cr00011a60010.1021/cr00011a600Search in Google Scholar
[6] Hrobáriková, V., Hrobárik, P., Gajdoš, P., Fitilis, I., Fakis, M., Persephonis, P., & Zahradník, P. (2010). Benzothiazolebased fluorophores of donor-π-acceptor-π-donor type displaying high two-photon absorption. The Journal of Organic Chemistry, 75, 3053–3068. DOI: 10.1021/jo100359q. http://dx.doi.org/10.1021/jo100359q10.1021/jo100359qSearch in Google Scholar
[7] Kiprianov, A. I., Stetsenko, A. V., & Sych, E. D. (1956). Cyanine dyes from the isomeric dimethylthiazolobenzothiazoles. Ukrainskii Khimichnii Zhurnal, 22, 760–766. Search in Google Scholar
[8] Kurtz, H. A., Stewart, J. J. P., & Dieter, K. M. (1990). Calculation of the nonlinear optical properties of molecules. Journal of Computational Chemistry, 11, 82–87. DOI: 10.1002/jcc.540110110. http://dx.doi.org/10.1002/jcc.54011011010.1002/jcc.540110110Search in Google Scholar
[9] Lakowicz, J. (1994). Probe design and chemical sensing. In J. R. Lakowicz (Ed.), Topics in fluorescence spectroscopy (Vol. 4, pp. 501–504). New York, NY, USA: Plenum Press. Search in Google Scholar
[10] Le Bouder, T., Massiot, P., & Le Bozec, H. (1998). Synthesis and coordination studies of new mono- and dihydroxy functionalized 4,4′-dialkenyl-2,2′-bipyridines. Tetrahedron Letters, 39, 6869–6872. DOI: 10.1016/s0040-4039(98)01499-3. http://dx.doi.org/10.1016/S0040-4039(98)01499-310.1016/S0040-4039(98)01499-3Search in Google Scholar
[11] Lee, C., Yang, W., & Parr, R. G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Reviews B, 37, 785–789. DOI: 10.1103/PhysRevB.37.785. http://dx.doi.org/10.1103/PhysRevB.37.78510.1103/PhysRevB.37.785Search in Google Scholar
[12] Lochon, P., Méheux, P., & Néel, J. (1967). Mono- and bisquaternary ammonium salts of dimethyl-2,6-benzobisthiazole-(1,2-5,4). Bulletin de la Société Chimique de France, 1967, 4387–4392. Search in Google Scholar
[13] Loudet, A., & Burgess, K. (2007). BODIPY dyes and their derivatives: Syntheses and spectroscopic properties. Chemical Reviews, 107, 4891–4932. DOI: 10.1021/cr078381n. http://dx.doi.org/10.1021/cr078381n10.1021/cr078381nSearch in Google Scholar
[14] Magdolen, P., Mečiarov Š. (2001). Ultrasound effect on the synthesis of 4-alkyl-(aryl)aminobenzaldehydes. Tetrahedron, 57, 4781–4785. DOI: 10.1016/s0040-4020(01)00403-3. http://dx.doi.org/10.1016/S0040-4020(01)00403-310.1016/S0040-4020(01)00403-3Search in Google Scholar
[15] Mike, J. F., Inteman, J. J., Ellern, A., & Jeffries-El, M. (2010). Facile synthesis of 2,6-disubstituted benzobisthiazoles: Functional monomers for the design of organic semiconductors. The Journal of Organic Chemistry, 75, 495–497. DOI: 10.1021/jo9023864. http://dx.doi.org/10.1021/jo902386410.1021/jo9023864Search in Google Scholar PubMed
[16] Mojzych, M., & Henary, M. (2008). Synthesis of cyanine dyes. In L. Strekowski (Ed.), Heterocyclic polymethine dyes: Synthesis, properties and applications (Topics in heterocyclic chemistry, Vol. 14, pp. 1–10). Berlin, Germany: Springer. Search in Google Scholar
[17] Schäfer, A., Huber, C., & Ahlrichs, R. (1994). Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr. The Journal of Chemical Physics, 100, 5829–5835. DOI: 10.1063/1.467146. http://dx.doi.org/10.1063/1.46714610.1063/1.467146Search in Google Scholar
[18] Semichem (2004). AMPAC 8.0 package [computer software]. Shawnee, KS, USA: Semichem, Inc. Search in Google Scholar
[19] Stewart, J. J. P. (1989a). Optimization of parameters for semiempirical methods I. Method. Journal of Computational Chemistry, 10, 209–220. DOI: 10.1002/jcc.540100208. http://dx.doi.org/10.1002/jcc.54010020810.1002/jcc.540100208Search in Google Scholar
[20] Stewart, J. J. P. (1989b). Optimization of parameters for semiempirical methods II. Applications. Journal of Computational Chemistry, 10, 221–264. DOI: 10.1002/jcc.540100209. 10.1002/jcc.540100209Search in Google Scholar
[21] Stewart, J. J. P. (1991). Optimization of parameters for semiempirical methods. III. Extension of PM3 to Be, Mg, Zn, Ga, Ge, As, Se, Cd, In, Sn, Sb, Te, Hg, Tl, Pb, and Bi. Journal of Computational Chemistry, 12, 320–341. DOI: 10.1002/jcc.540120306. http://dx.doi.org/10.1002/jcc.54012030610.1002/jcc.540120306Search in Google Scholar
[22] Treutler, O., & Ahlrichs, R. (1995). Efficient molecular numerical integration schemes. The Journal of Chemical Physics, 102, 346–354. DOI: 10.1063/1.469408. http://dx.doi.org/10.1063/1.46940810.1063/1.469408Search in Google Scholar
[23] Turbomole (2010). TURBOMOLE version 6.2 [computer software]. Karlsruhe, Germany: Turbomole GmbH. Search in Google Scholar
[24] Zhang, X. H., Chen, B. J., Lin, X. Q., Wong, O. Y., Lee, C. S., Kwong, H. L., Lee, S. T., & Wu, S. K. (2001). A new family of red dopants based on chromene-containing compounds for organic electroluminescent devices. Chemistry of Materials, 13, 1565–1569. DOI: 10.1021/cm0008664. http://dx.doi.org/10.1021/cm000866410.1021/cm0008664Search in Google Scholar
© 2012 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
- Professor Dr. Štefan Toma—excellent scientist and teacher—celebrates his 75th birthday
- Palladium-catalysed Claisen rearrangement of 6-allyloxypurines
- Applicability of photochemically generated pendant benzoyl peroxides in both “grafting from” and “grafting to” techniques
- Spectral characterisation of new organic fluorescent dyes with an alkoxysilane moiety and their utilisation for the labelling of layered silicates
- Substituted homoallenyl aldehydes and their derivatives. Part 1: Homoallenyl aldehydes and protected hydrazones
- Substituted homoallenyl aldehydes and their derivatives. Part 2: Azines
- Methyltrioxorhenium-catalysed oxidation of secondary amines to nitrones in ionic liquids
- Thiophenium-ylides: Synthesis and reactivity
- Aminohydroxylation of divinylcarbinol and its application to the synthesis of bicyclic hydroxypyrrolidine and aminotetrahydrofuran building blocks
- Novel quercetin derivatives: synthesis and screening for anti-oxidant activity and aldose reductase inhibition
- Total synthesis of N,O,O,O-tetraacetyl-d-ribo-phytosphingosine and its 2-epi-congener
- A concise synthesis of enantiomerically pure aroyl-l-alanines and dihydroaroyl-l-alanines
- Synthesis and properties of macrocyclic diazene switch with binaphthalene unit attached via acrylamide linkers
- Conjugated push-pull salts derived from linear benzobisthiazole: preparation and optical properties
- Effect of reactants’ concentration on the ratio and yield of E,Z isomers of isatin-3-(4-phenyl)semicarbazone and N-methylisatin-3-(4-phenyl)semicarbazone
Articles in the same Issue
- Professor Dr. Štefan Toma—excellent scientist and teacher—celebrates his 75th birthday
- Palladium-catalysed Claisen rearrangement of 6-allyloxypurines
- Applicability of photochemically generated pendant benzoyl peroxides in both “grafting from” and “grafting to” techniques
- Spectral characterisation of new organic fluorescent dyes with an alkoxysilane moiety and their utilisation for the labelling of layered silicates
- Substituted homoallenyl aldehydes and their derivatives. Part 1: Homoallenyl aldehydes and protected hydrazones
- Substituted homoallenyl aldehydes and their derivatives. Part 2: Azines
- Methyltrioxorhenium-catalysed oxidation of secondary amines to nitrones in ionic liquids
- Thiophenium-ylides: Synthesis and reactivity
- Aminohydroxylation of divinylcarbinol and its application to the synthesis of bicyclic hydroxypyrrolidine and aminotetrahydrofuran building blocks
- Novel quercetin derivatives: synthesis and screening for anti-oxidant activity and aldose reductase inhibition
- Total synthesis of N,O,O,O-tetraacetyl-d-ribo-phytosphingosine and its 2-epi-congener
- A concise synthesis of enantiomerically pure aroyl-l-alanines and dihydroaroyl-l-alanines
- Synthesis and properties of macrocyclic diazene switch with binaphthalene unit attached via acrylamide linkers
- Conjugated push-pull salts derived from linear benzobisthiazole: preparation and optical properties
- Effect of reactants’ concentration on the ratio and yield of E,Z isomers of isatin-3-(4-phenyl)semicarbazone and N-methylisatin-3-(4-phenyl)semicarbazone