Abstract
The review deals with the special type of the organic molecules which contain the collective system of π-electrons; the mobility of the electrons that determines both the electron structure and spectral properties of considered conjugated molecules. The classification of the linear conjugated systems is proposed: polymethine dyes, polyenes, donor-acceptor compounds and the differences between them. It is shown that the high mobility of the collective π-electron shell depends on the type of the conjugated system, chain length, symmetry, molecular constitution of the terminal groups, as well as the electron shell (neutral or charge system). Experimentally, the features of the electron structure of conjugated molecules are observed by spectral methods, especially, in various solvents. It is established that different molecular types show the different sensitivity to the solvent polarity. The work reviews principal results that were obtained by the quantum-chemical and spectral study of the linear conjugated systems.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
S. Daehne, Color and constitution. One hundred years of research. Science 199, 1163–116
S. Daehne, K. Hoffmann, Colour and constitution: linear free energy relationships and/or polymethinic colour rules. J. Mol. Str. 219, 403–409 (1990). https://doi.org/10.1016/0022-2860(90)80089-3
S. Daehne, Der ideale Polymethin zustand. Chimia 45, 288–296 (1991). DOI: 200901100400230156
G. Bach, S. Daehne, Cyanine dyes and related compounds, in ROOD’S Chemistry of Carbon Compounds, 2nd suppl. to 2nd edn., vol. IVB, chapter 15, Heterocyclic Compounds, ed. by, M. Sainsbury (Elsevier Science, Amsterdam, 1997), pp. 383–481
A. Mishra, R.K. Behera, P.K. Behera, B.K. Mishra, G.B. Behera, Cyanine during the 1990s: a review. Chem. Rev. 100, 1973–2011 (2000). https://doi.org/10.1021/cr990402t
G. Orlandi, F. Zerbetto, M.Z. Zgierski, Theoretical analysis of spectra of short polyenes. Chem. Rev. 91, 867–891 (1991). https://doi.org/10.1021/cr00005a012
A.D. Kachkovsky, The nature of electronic transitions in linear conjugated systems. Russ. Chem. Rev. 66, 647–664 (1997). https://doi.org/10.1070/RC1997v066n08ABEH000274
J.L. Bricks, A.D. Kachkovskii, Yu.L. Slominskii, A.O. Gerasov, S.V. Popov, Molecular design of near infrared polymethine dyes: a review. Dyes Pigments 121, 238–255 (2015). https://doi.org/10.1016/j.dyepig.2015.05.016
H. Kuhn, A Quantum-mechanical theory of light absorption of organic dyes and similar compounds. J. Chem. Phys. 17, 1098–1212 (1949). https://doi.org/10.1063/1.1747143
N.S. Bayliss, A “metalic” model for the spectra of conjugated polyenes. J. Chem. Phys. 16, 287–292 (1948). https://doi.org/10.1021/bk-2013-1122.ch004
J.R. Platt, Wavelength formulas and configuration interaction in Brooker dyes and chain molecules. J. Chem. Phys. 25, 80–105 (1956). https://doi.org/10.1063/1.1742852
M.L. Dekhtyar, Application of the quasi-long chain approximation to structural perturbation in polymethine dyes. Dyes & Pigments 28, 261–274 (1995). https://doi.org/10.1016/0143-7208(95)00065-8
J. Fabian, TDDFT-calculations of Vis/NIR absorbing compounds. Dyes Pigments 84, 36–53 (2010). https://doi.org/10.1016/j.dyepig.2009.06.008
S. Karaca, N. Elmaci, A computational study on the excited state properties of a cationic cyanine dye: TTBC. Comput. Theoret. Chem 964, 160–168 (2011). https://doi.org/10.1016/j.comptc.2010.12.016
W.P. Su, J.R. Schrieffer, A.J. Heeger, Solitons in polyacetylene. Phys. Rev. Lett. 42, 1698–1701 (2011). https://doi.org/10.1103/physrevlett.42.1698
W.P. Su, J.R. Schrieffer, A.J. Heeger, Solitons excitations in polyacetylene. Phys. Rev. 22, 2099–2111 (1980). https://doi.org/10.1103/PhysRevB.22.2099
L.M. Tolbert, The photoexcited states of allyl anions. Acc. Chem. Res. 19, 268–273 (1986). https://doi.org/10.1021/ar00129a002
L.M. Tolbert, Solitons in a box: the organic chemistry of electrically conducting polyenes. Acc. Chem. Res. 25, 561–568 (1992). https://doi.org/10.1021/ar00024a003
A.D. Kachkovskii, The solitonic nature of ions of linear conjugated systems. Theoret. Exp. Chem. 41, 139–164 (2005). DOI: 0040-5760/05/4103-0139
F.M. Hamer, Cyanine Dyes and Related Compounds (Interscience, New York, 1964), 790 pp.
A.V. Kulinich, A.A. Ishchenko, Merocyanine dyes: synthesis, structure, properties and applications Russ. Chem. Rev. 78, 141–164 (2009). https://doi.org/10.1070/RC2009v078n02ABEH003900
A.V. Kulinich, N.A. Derevyanko, E.K. Mikitenko, A.A. Ishchenko, Merocyanines based on 1,3ω-indanedione: electronic structure and solvatochromism. J. Phys. Org. Chem. 24, 732–742 (2011). https://doi.org/10.1002/poc.1821
H. Mustroph, K. Reiner, B. Senns, J. Mistol, S. Ernst, D. Keil, L. Hennig, The effects of substituents and solvents on the ground-state π-electronic structure and electronic absorption spectra of a series of model merocyanine dyes and their theoretical interpretation. Chem. Eur. J. 18, 8140–8149 (2012). https://doi.org/10.1002/chem.201101830
J. Bricks, J. Slominskii, M. Kudinova, Syntheses and photophysical properties of a series of cation-sensitive polymethine and styryl dyes. J. Photochem. Photobiol. A: Chem. 132, 193–208 (2000). https://doi.org/10.1016/S1010-6030(00)00208-2
L. Brooker, G. Keyes, R. Sprague, Studies in the cyanine dye series. XI. The merocyanines. J. Am. Chem. Soc. 73, 5326–5332 (1951). https://doi.org/10.1021/ja01155a095
N.V. Pilipchuk, G.O. Kachkovsky, Yu.L. Slominskii, O.D. Kachkovsky, Electronic properties of polymethine systems. 11. Absorption spectra and nature of cationic oxystyryl and their neutral derivatives. Dyes Pigments 71(1), 1–9 (2006). https://doi.org/10.1016/j.dyepig.2005.04.013
B.I. Shapiro, Molecular assemblies of polymethine dyes. Russ. Chem. Rev. 75(5), 484–510 (2006). https://doi.org/10.1070/RC2006v075n05ABEH001208
F. Wurthner, T.E. Kaiser, C.R. Saha-Muller, J-Aggregates: from serendipitous discovery to supramolecular engineering of functional dye materials. Angew. Chem. Int. Ed. 50, 3376–3410 (2011). https://doi.org/10.1002/anie.201002307
Y.I. Prylutskyy, V.V. Cherepanov, M.P. Evstigneev, O.A. Kyzyma, V.I. Petrenko, V.I. Styopkin, L.A. Bulavin, N.A. Davidenko, D. Wyrzykowski, A. Woziwodzka, J. Piosik, R. Kaźmierkiewicz, U. Ritter, Structural self-organization of C60 and cisplatin in physiological solution. Phys. Chem. Chem. Phys. 17(39), 26084–26092 (2015). https://doi.org/10.1039/c5cp02688a.2
Y.I. Prylutskyy, M.P. Evstigneev, V.V. Cherepanov, O.A. Kyzyma, L.A. Bulavin, N.A. Davidenko, P. Scharff, Structural organization of C60 fullerene, doxorubicin, and their complex in physiological solution as promising antitumor agents. J. Nanopart. Res. 17, 45 (2015). https://doi.org/10.1007/s11051-015-2867-y
O.A. Kyzyma, T.O. Kyrey, M.V. Avdeev, M.V. Korobov, L.A. Bulavin, V.L. Aksenov, Non-reversible solvatochromism in N-methyl-2-pyrrolidone/toluene mixed solutions of fullerene C60. Chem. Phys. Lett. 556, 178–181 (2013). https://doi.org/10.1016/j.cplett.2012.11.040
L.G.S. Brooker, Spectra of dye molecules. Absorbtion and resonance in dyes. Rev. Mod. Phys. 14, 275–293 (1942). https://doi.org/10.1103/revmodphys.14.275
S. Huenig, H. Berneth, Two step reversible redox systems of the weitz type. Top. Curr. Chem. 92, 1–44 (1980). https://doi.org/10.1007/BFb0034356
A.D. Kachkovskii, D.A. Yushchenko, G.A. Kachkovskii, Breaking of symmetry of solitons in the ion-radicals of α,ω-disubstituted polyenes. Teor. Éksp. Khim. 38(6), 341–346 (2002). https://doi.org/10.1023/a:102221960
A.D. Kachkovskii, D.A. Yushchenko, G.A. Kachkovskii, D.M. Shut, Electronic properties of polymethine systems. 8. Geometry and electron structure of radicals. Dyes Pigments 66, 211–221 (2005). https://doi.org/10.1016/j.dyepig.2004.06.020
H. Oeling, F. Baer, Radikaleaus Polymethin-Farbstoffen: III—Polymethinoxonole. Org. Magn. Reson. 8, 623–627 (1976). https://doi.org/10.1002/mrc.1270081207
J.L. Bredas, G.B. Street, Polaron, bipolaron and solitons in conducting polymers. Acc. Chem. Res. 18, 309–315 (1985). https://doi.org/10.1021/ar00118a005
A.O. Gerasov, I.H. Nayyar, A.E. Masunov, O.V. Przhonska, O.D. Kachkovsky, D.O. Melnyk, O.B. Ryabitsky, O.O. Viniychuk, Solitonic waves in polyenedications and principles of charge carrier localization in π-conjugated organic materials. Int. J. Quant. Chem. 112, 2659 (2012). https://doi.org/10.1002/qua.23281
O.S. Nechyporenko, O.P. Melnyk, O.O. Viniychuk, T.M. Pinchuk-Rugal, V.A. Brusentsov, E.L. Pavlenko, Shape and location of multiple charge carriers in linear p-electron systems. Int. J. Quant. Chem. 114, 416–428 (2014). https://doi.org/10.1002/qua.24585
A.E. Masunov, D. Anderson, A.Ya. Freidzon, A.A. Bagaturyants, Symmetry-breaking in cationic polymethine dyes: Part 2. Shape of electronic absorption bands explained by the thermal fluctuations of the solvent reaction field. J. Phys. Chem. A 119 (26), 6807–6815 (2015). https://doi.org/10.1021/acs.jpca.5b03877
M. Ikai, S. Tokito, Highly efficient phosphorescence from organic light-emitting devices with an exciton-block layer. Appl. Phys. Lett. 79, 156–158 (2001). https://doi.org/10.1063/1.1385182
F. Koehn, J. Hofkens, R. Gronheid, M. Van der Auweraer, F.C. De Schryver, Parameters influencing the on- and off-times in the fluorescence intensity traces of single cyanine dye molecules. J. Phys. Chem. A 106(19), 4808–4814 (2002). https://doi.org/10.1021/jp012959u
P.F.H. Schwab, J.R. Smith, J. Michl, Synthesis and properties of molecular rods. 2. Zig-Zag rods. Chem. Rev. 105, 1197–279 (2005). https://doi.org/10.1021/cr040707u
D. Valeur, Principles of fluorescent probe design for ion recognition, in Topics in Fluorescence Spectroscopy. Probe Design and Chemical Sensing, vol. 4, ed. by, J.R. Lacowicz (New York, Plenum, 1994), pp. 21–48
G. Patonay, J. Salon, J. Sowell, L. Strekowski, Noncovalent labeling of bio-molecules with red and near-infrared dyes. Molecules 9, 40–49 (2004). https://doi.org/10.3390/90300040
S.M. Borisov, O.S. Wolfbeis, Optical biosensors. Chem. Rev. 108, 423–461 (2008). https://doi.org/10.1021/cr068105t
M.Y. Berezin, S. Achilefu, Fluorescence lifetime measurements and biological imaging. Chem. Rev. 110(5), 2641–2684 (2010). https://doi.org/10.1021/cr900343z
H. Kobayashi, M. Ogawa, R. Alford, P.L. Choyke, Ya. Urano, New strategies for fluorescent probe design in medical diagnostic imaging. Chem. Rev. 110, 2620–2640 (2010). https://doi.org/10.1021/cr900263j
A. Cravino, P. Leriche, O. Aleveque, S. Roquet, J. Roncali, Light-emitting organic solar cells based on a 3D conjugated system with internal charge transfer. Adv. Mater. 18, 3033–3037 (2006). https://doi.org/10.1002/adma.200601230
Yo. Ooyama, Yu. Harima, Designs and syntheses of organic dyes for dye-sensitized solar cells. Eur. J. Org. Chem. 18, 2903–2934 (2009). https://doi.org/10.1002/ejoc.200900236
G. Chen, D. Yokoyama, H. Sasabe, Z. Hong, Y. Yang, J. Kido, Optical and electrical properties of a squaraine dye in photovoltaic cells. Appl. Phys. Lett. 101(8), 083904 (2012). https://doi.org/10.1063/1.4747623
O.V. Przhonska, J. Lim, D.J. Hagan, E.W. Van Stryland, M.V. Bondar, Yu.L. Slominsky, Nonlinear light absorption of polymethine dyes in liquid and solid media. J. Opt. Soc. Am. B. 15(2), 802–809 (1998). https://doi.org/10.1364/josab.15.000802
W. Zhou, S.M. Kuebler, K.L. Braun, T.Yu.J.K. Cammack, C.K. Ober, J.W. Perry, S.R. Marder, An efficient two-photon-generated photoacid applied to positive-tone 3D microfabrication. Science 96(5570), 1106–1109 (2002). https://doi.org/10.1126/science.296.5570.1106
S.R. Marder, Organic nonlinear optical materials: where we have been and where we are going. Chem. Commun. 2, 131–134 (2006). https://doi.org/10.1039/b512646k
F. Terenziani, G. D’Avino, A. Painelli, Multichromophores for nonlinear optics: designing the material properties by electrostatic interactions. Chem. Phys. Phys. Chem. 8(17), 2433–2444 (2007). https://doi.org/10.1002/cphc.200700368
M.G. Kuzyk, Using fundamental principles to understand and optimize nonlinear-optical materials. J. Mater. Chem. 19, 7444–7465 (2009). https://doi.org/10.1039/b907364g
O.V. Przhonska, S. Webster, L.A. Padilha, H. Hu, A.D. Kachkovskii, D.J. Hagan, E.W. Van Stryland, Two-photon absorption in near-IR conjugated molecules: design strategy and structure-property relations, in Advanced Fluorescence Reporters in Chemistry and Biology I. Springer Series Fluorescence (Springer, Berlin, Heidelberg, 2010), pp. 105–148. https://doi.org/10.1007/978-3-642-04702-2_4
J. Griffiths, Colour and Constitution of Organic Molecules (Academic Press, London, 1976), 281 pp. https://doi.org/10.1002/col.5080030213
O. Ye, S.M. Shaydyuk, S.A. Levchenko, D. Kurhuzenkau, A.E. Anderson, O.D. Masunov, Yu.L. Kachkovsky, J.L. Slominsky, K.D. Bricks, M.V. Belfield, Bondar linear photophysics, two-photon absorption and femtosecond transient absorption spectroscopy of styryl dye bases. J. Lum. 183, 360–367 (2017). https://doi.org/10.1016/j.jlumin.2016.11.073
K. Rurack, Flipping the light switch “ON”—the design of sensor molecules that show cation-induced fluorescence enhancement with heavy and transition meta ions. Spectrochim. Acta A Mol. Biomol. Spectrosc. 57(11), 2161–2195 (2001). https://doi.org/10.1016/S1386-1425(01)00492-9
C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 3rd edn. (Wiley-VCH, Weinheim, 2003), 653 pp. ISBN 978–3-527-60567-5
F.L. Arbeloa, T.L. Arbeloa, I.L. Arbeloa, Electronic spectroscopy of pyrromethene. J. Photochem. Photobiol. A: Chem. 121, 177–182 (1999). https://doi.org/10.1016/S1010-6030(98)00453-5
A. Toutchkine, W.-G. Han, M. Ullmann, T. Liu, D. Bashford, L. Noodleman, K.M. Hahn, Experimental and DFT studies: novel structural modifications greatly enhance the solvent sensitivity of live cell imaging dyes. J. Phys. Chem. A 111, 10849–10860 (2007). https://doi.org/10.1021/jp073197r
M.A. Kudinova, N.A. Derevyanko, G.G. Dyadyusha, A.A. Ishchenko, A.I. Tolmachev, Pyrylocyanines. Symmetrical tetraphenyl-substituted pyrylo-2-cyanines. Chem. Het. Comp. 16(7), 691–695 (1980). https://doi.org/10.1007/bf00557737
A.I. Tolmachev, N.A. Derevyanko, A.A. Ishchenko, Pyrylocyanines. 16. Tetraphenyl-substituted (pyrylo-2) (pyrylo-4) cyanines. Chem. Het. Comp. 18(9), 897–902 (1982). https://doi.org/10.1007/bf00513426
K. Zyabrev, A. Doroshenko, E. Mikitenko, Yu. Slominskii, A. Tolmachev, Design, synthesis, and spectral luminescent properties of a novel polycarbocyanine series based on the 2,2-difluoro-1,3,2-dioxaborine nucleus. Eur. J. Org. Chem. 9, 1550–1558 (2008). https://doi.org/10.1002/ejoc.200701012
P. Bouit, C. Aronica, L. Toupet, B.L. Guennic, C. Andraud, O. Maury, Continuous symmetry breaking induced by ion pairing effect in heptamethine cyanine dyes: beyond the cyanine limit. J. Am. Chem. Soc. 132(12), 4328–4335 (2010). https://doi.org/10.1021/ja9100886
J. Fabian, Symmetry-lowering distortion of near-infrared polymethine dyes—a study by first-principles methods. J. Mol. Struct.: THEOCHEM 766, 49–60 (2006). https://doi.org/10.1016/j.theochem.2006.02.003
F. Terenziani, A. Painelli, C. Katan, M. Charlot, M. Blanchard-Desce, Charge instability in quadrupolar chromophores: symmetry breaking and solvatochromism. J. Am. Chem. Soc. 128(49), 15742–15755 (2006). https://doi.org/10.1021/ja064521j
S.V. Vasyluk, O.O. Viniychuk, Ye.M. Poronik, Yu.P. Kovtun, M.P. Shandura, V.M. Yashchuk, O.D. Kachkovsky, Breaking of symmetrical charge distribution in xanthylocyanine chromophores detecting by their absorption spectra. J. Mol. Struct. 990, 6–13 (2011). DOI: 10.1016/j.molstruc.2010.12.047
A.D. Kachkovskii, A.I. Tolmachev, Yu.L. Slominskii, M.A. Kudinova, N.A. Derevyanko, O.O. Zhukova, Electronic properties of polymethine systems. 7. Soliton symmetry breaking and spectral features of dyes with a long chain. Dyes Pigments 64, 207–217 (2005). https://doi.org/10.1016/j.dyepig.2004.04.003
R.S. Lepkowich, O.V. Przhonska, J.M. Hales, D.J. Hagan, E.W. Van Sryland, M.V. Bondar, Nature of electron transitions in thiacyanines with a long polymethine chain. Chem. Phys. 305, 259–270 (2004). https://doi.org/10.1016/j.chemphys.2004.06.063
F. Terenziani, O.V. Przhonska, S. Webster, L.A. Padilha, Yu.L. Slominsky, I.G. Davydenko, A.O. Gerasov, YuP Kovtun, M.P. Shandura, A.D. Kachkovskii, J.D. Hagan, E.W. Van Stryland, A. Painelli, Essential-state model for polymethine dyes: symmetry breaking and optical spectra. J. Phys. Chem. Lett. 1, 1800–1804 (2010). https://doi.org/10.1021/jz100430x
G.T. Dempsey, M. Bates, W.E. Kowtoniuk, D.R. Liu, R.Y. Tsien, X. Zwuang, Photoswitching mechanism of cyanine dyes. J. Am. Chem. Soc. 131(51), 18192–18193 (2009). https://doi.org/10.1021/ja904588g
S.V. Vasyluk, V.M. Yashchuk, O.O. Viniychuk, Yu.P. Piryatinskii, M.M. Sevryukova, A.O. Gerasov, The investigation of relaxation paths in oxyborine anionic polymethine dyes detected by low-temperature time-resolved fluorescence. Mol. Cryst. Liq. Cryst. 535, 123–131 (2011). https://doi.org/10.1080/15421406.2011.537959
P. Lutsyk, Yu. Piryatinski, O. Kachkovsky, A. Verbitsky, A. Rozhin, Unsymmetrical relaxation paths of the excited states in cyanine dyes detected by time-resolved fluorescence: polymethinic and polyenic forms. J. Phys. Chem. A 121(43), 8236–8246 (2017). https://doi.org/10.1021/acs.jpca.7b08680
A.V. Stanova, A.B. Ryabitsky, V.M. Yashchuk, O.D. Kachkovsky, A.O. Gerasov, Ya.O. Prostota, O.V. Kropachev, Asymmetry in ground and excited states in styryls and methoxystyryls detected by NMR (13 C), absorption, fluorescence and fluorescence excitation spectroscopy. J. Mol. Struct. 988, 102–110 (2011). https://doi.org/10.1016/j.molstruc.2010.12.038
M. Henary, A. Levitz, Synthesis and applications of unsymmetrical carbocyanine dyes. Dyes Pigments 99, 1107–1116 (2013). https://doi.org/10.1016/j.dyepig.2013.08.001
PYu. Kobzar, E.L. Pavlenko, V.A. Brusentsov, O.P. Dmytrenko, N.P. Kulish, J.L. Bricks, Yu.L. Slominskii, V.V. Kurdyukov, O.I. Tolmachev, O.D. Kachkovsky, Comparative study of electronic structure cyanine bases versus parent cationic cyanines. J. Adv. Phys. 6, 334–345 (2017). https://doi.org/10.1166/jap.2017.1347
E.L. Pavlenko, O.P. Dmytrenko, M.P. Kulish, V.V. Kurdyukov, O.I. Tolmachev, A.D. Kachkovsky, Spectral and quantum-chemical studies of the band shape in absorption of merocyanine derivatives of cyclohexadienone. J. Adv. Phys. 6(4), 514–523 (2017). https://doi.org/10.1166/jap.2017.1365
A.D. Kachkovsky, N.V. Pilipchuk, V.V. Kurdyukov, A.I. Tolmachev, Electronic properties of polymethine systems. 10. Electron structure and absorption spectra of cyanine bases. Dyes Pigments 70, 212–219 (2006). https://doi.org/10.1016/j.dyepig.2004.12.011
H. Mustroph, J. Mistol, B. Senns, D. Keil, M. Findeisen, L. Hennig, Relationship between the molecular structure of merocyanine dyes and the vibrational fine structure of their electronic absorption spectra. Angew. Chem. Int. Ed. 48, 8773–8775 (2009). https://doi.org/10.1002/anie.200902687
A. Sanchez-Galvez, P. Hunt, M.A. Robb, M. Olivucci, T. Vreven, H.B. Schlegel, Ultrafast radiationless deactivation of organic dyes: evidence for a two-state two-mode pathway in polymethine cyanines. J. Am. Chem. Soc. 122(12), 2911–2924 (2000). https://doi.org/10.1021/ja993985x
M.V. Bondar, N.A. Derevyanko, G.G. Dyadyusha, A.A. Ishchenko, Generation of light in the near infrared using solutions of asymmetric polymethine dyes. Sov. J. Quant. Electron. 14(3), 317–322 (1984). https://doi.org/10.1070/qe1984v014n03abeh004888
Yu.L. Briks, Yu.A. Nesterenko, A.I. Tolmachev, A.D. Kachkovskii, Synthesis and spectral properties of vinylogs of heterylpolyenes based on pyran. Chem. Het. Comp. 26(2), 218–221 (1990). https://doi.org/10.1007/bf00499420
O.M. Navozenko, A.P. Naumenko, V.M. Yashchuk, J.L. Bricks, Yu.L. Slominskii, A.B. Ryabitskii, O.D. Kachkovsky, Nature of the lowest electron transitions in styryl bases benzothiazole derivatives and analogues bearing para-methoxy and -trifluoromethyl substituents in phenylyne moiety. J. Mol. Struct. 1113, 32–41 (2016). https://doi.org/10.1016/j.molstruc.2016.01.062
Acknowledgements
Figures 9.2, 9.4 and 9.3, Table 9.1 are reprinted from: [8, 81]; Table 9.6 is reprinted from A.D. Kachkovsky, N.V. Pilipchuk, V.V. Kurdyukov, A.I. Tolmachev, Yu.L. Slominskii, V.Ya. Gayvoronsky, E.V. Shepelyavyy, S.V. Yakunin, M.S. Brodyn, Spectral and non-linear optical properties of cyanine bases’ derivatives of benzo[c, d]indole, Dyes Pigments 74, 195–201 (2007) https://doi.org/10.1016/j.dyepig.2006.01.048, respectively with permission from Elsevier.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2019 Springer Nature Switzerland AG
About this paper
Cite this paper
Pavlenko, O.L. et al. (2019). Electron Structure and Optical Properties of Conjugated Systems in Solutions. In: Bulavin, L., Xu, L. (eds) Modern Problems of the Physics of Liquid Systems. PLMMP 2018. Springer Proceedings in Physics, vol 223. Springer, Cham. https://doi.org/10.1007/978-3-030-21755-6_9
Download citation
DOI: https://doi.org/10.1007/978-3-030-21755-6_9
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-21754-9
Online ISBN: 978-3-030-21755-6
eBook Packages: Physics and AstronomyPhysics and Astronomy (R0)