Fig. 3. Morse curves for the ground ( a ) and excited state ( b ) of a diatomic molecule2) Fig. 2. The various modes of energy dissipation from electr

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1 Color and Constitution of Organic Colorants, and Some Approach to New Chromophore Masaru MATSUOKA

2 Fig. 3. Morse curves for the ground ( a ) and excited state ( b ) of a diatomic molecule2) Fig. 2. The various modes of energy dissipation from electronically excited states a. Internal conversion, b. Intersystem crossing, c. Fluorescence, d. Phosphorescence2)

3 Fig. 4. vma. of 2-R-anthraquinone versus I. P of CH3-R4) Scheme-I. Schematic representation of Donor -Acceptor chromogen2) Fig. 5. Substituent effects of Malachite Green 28)

4 Table 1. Absorption spectra of some donor-acceptor substituted azobenzenes2) Table 2. Substituent effects of indigo and thioindigo derivatives

5 Scheme-3. Red quinophthalone pigments

6 Scheme-4. Fig. 6. Absorption and fluorescence spectra of naphthalimide and reflectance curve (A) with and (B) without fluorescence excitation of 8' ) Fig. 7. Reflectance curves without Fluorescent Whitening Agent (FWA) ( a ), and with FWA (d : true reflectance, f : total reflectance. e : Fluorescence curve of FWA.)

7 Fig. 8. Effect of a polar solvent on the transition energy of a molecule ; ( a ) situation in the vapour phase, or in non-polar solvents ; ( b ) ground state more polar than excited state ; ( c ) ground state less polar than excited state2)

8 Table 3. Absorption maxima and dominant tautomeric forms for some azo-hydrazone systems2) Scheme-52).

9 Fig.. 9. Effect of bond rotation on the ground and excited state of a molecule, a: planar situation, b: increased bond order in the excited state, c : reduced bond order in the excited state2) Scheme-62).

10 Scheme-7. 21)

11 Scheme-8. Changes in 7r-electron density accompanying first excitation of 1-aminoanthraquinone, -I- sign indicates an increase in 7r-electron density2)

12 Fig. 10. Linear relationship between calculated and observed Amax") Scheme-9. LCAO coefficients of 1-aminoAQ, AQ and aniline

13 Scheme-10. Changes in ir-electron density accompanying the first excitation and the characters of the intramolecular charge transfer") Fig. 11. Relationship between annelation effect (44E1) and 4E1 parent23) Table 4. Effects of intermolecular hydrogen bonding with the quinone carbonyl groups on the first excitation energy 4E1 and the oscillator strength fi of 1-amino- and 2-aminoanthraqunone (AQ)S16)

14 Scheme-11. Comparison of HOMO-LUMO level between anthraquinones (AQ) and naphthoquinones (NQ) Fig. 12. Relationship between 4E1 and JEmax of azo dyes19)

15 Table 5. Substituent effects of azobenzene derivatives") 2) J. Griffiths : "Colour and Constitution of Organic Molecules", Academic Press London, ) Z. Yoshida, F. Takabayashi : Tetrahedron, 24, 933 (1968) 5) R. S. Sinclair, E. McAlpine : J. Soc. Dyers and Colourists, 91, 399 (1975) 6) M. Matsuoka, M. Kishimoto, T. Kitao : ibid, 94, 435 (1978) 7) H. Ionue, T. Hoshi, J. Yoshino, Y. Tanizaki : Bull. Chem. Soc. Japan, 45, 1018 (1972) 8) C. C. Barker, M. H. Bride, G. Hallas, A. Stamp : J. Chem. Soc., 1961, ) B. L. Kaul : Hely. Chim. Acta, 57, 2664(1974) 10) P. Moeckli : Dyes and Pigments, 1, 3 (1980) 13) Teijin : Japan Kokai, 78-56, ) W. West, S. Pearce : J. Phys. Chem., 69, 1894 (1965) 15) E. J. Land, E. McAlpine, R. S. Sinclair, T. G. Truscott : J. Soc. Dyers and Colourists, 92, 233 (1976) 16) Y. Kogo, H. Kikuchi, M. Matsuoka, T. Kitao : ibid, 96, 475 (1980) 17) J. Rocklitz : Chimia, 34, 131 (1980) IL D. Scharf et al.: Angew. Chem. Int. Ed. Engl., 18, 652 (1979) 18) A. W. Adamson : Chem. Engineering, Jan. 28 (1980), p.59.

16 21) K. Nakanishi et al.: J. Am. Chem. Soc., 101, 7082, 7084, 7086 (1979) :22) R. Pariser, R. G. Parr : J. Chem. Phys., 21, 466, 767 (1953) J. A. Pople : Trans. Faraday Soc., 49, 1375 (1953) 23) Y. Kogo, H. Kikuchi, M. Matsuoka, T. Kitao : J. Soc. Dyers and Colourists, 96, 526 (1980) 24) H. Nakazumi, T. Agawa, T. Kitao : Bull. Chem. Soc. Japan, 52, 2445 (1979) 25) G. G. Buckley, J. Griffiths : J. Chem. Soc. Perkin I, 1979, ) J. Fabian : J. Signal AM, 6, 307 (1978), 7, 67 (1979), idem, J. prak. Chem., 320, 361 (1978), 321, 499 (1979), 322, 1 (1980) 28) J. Fabian, H. Hartmann : "Light Absorption of Organic Colorants" Sprinnger-Verlag, Berlin, 1980.

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