Design, synthesis, and evaluation of a dye library: Glass-forming and solid-state luminescent merocyanines for functional materials

Angewandte Chemie - International Edition

Volumn 38, Issue 11, 1999, Pages 1649-1652

  Würthner, Frank ^a,b   Sens, Rüdiger ^a   Etzbach, Karl Heinz ^a   Seybold, Günther ^a  

^a BASF SE   (Germany)

^b UNIVERSITY OF ULM   (Germany)

Author keywords

Combinatorial chemistry; Dyes; Luminescence; Multicomponent reactions; Polymethines

Indexed keywords

AMPHOLYTE; DYE; GLASS; MEROCYANINE;

ALKYLATION; ARTICLE; CRYSTALLIZATION; DIPOLE; HYDROLYSIS; LIGHT REFRACTION; LUMINESCENCE; PHYSICAL CHEMISTRY; POLARIZATION; POLYMERIZATION; REACTION ANALYSIS; SOLID STATE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037839543     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990601)38:11<1649::AID-ANIE1649>3.0.CO;2-H     Document Type: Article

References (21)

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3. P. Gregory, High-Technology Applications of Organic Colorants, Plenum, New York, 1991.
4. Brilliant hues are obtained when only one absorption band, which additionally has to be as narrow as possible, appears in the visible spectral range. For four-color printing, a medium color component -magenta - with an absorption band between 520 and 550 nm is required.
5. R. W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown, T. A. Keating, Acc. Chem. Res. 1996, 29, 123-131.
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11. F. Würthner, unpublished results.
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14. In numerous reactions, starting materials with purities (NMR, GC) <80% were used and nevertheless very good yields were obtained and pure products isolated. Difficulties were encountered with the most readily soluble dyes when these did not crystallize from the reaction mixtures in the presence of solubility-promoting impurities or when greater amounts of 2-propanol, which became necessary in the washing procedure, led to losses in yield.
15. Because of the high influence of the purity on the investigated properties (see Tables 1 and 2), the dyes were recrystallized once more.
16. H. K. Cammenga, M. Epple, Angew. Chem. 1995, 107, 1284-1301, Angew. Chem. Int. Ed. Engl. 1995, 34, 1171.
17. H. K. Cammenga, M. Epple, Angew. Chem. 1995, 107, 1284-1301, Angew. Chem. Int. Ed. Engl. 1995, 34, 1171.
18. Although the glassy state is regarded as a typical feature of polymeric substances, great progress was recently achieved by using low molecular weight organic glasses in the development of photoconductive and electroluminescent materials: a) K.-Y. Law, Chem. Rev. 1993, 93, 449-486;
19. b) J. Salbeck, Ber. Bunsen-Ges. Phys. Chem. 1996, 100, 1667-1677.
20. Compounds of the structural types 4-6 also show intensive luminescence in solid solutions, that is in textile dyeing on polyester. A detailed discussion of the competition between radiationless deactivation and photoluminescence, which is evidently strongly dependent on the rigidity of the matrix, should become possible based on the emission spectra of solid samples and dyed textile fibers as well as on crystal structure analyses.
21. As extremely small concentrations of impurities already function as traps in the solid state, the data given in Tables 1 and 2 should not be overinterpreled. Especially the substances marked (+) could show better emission properties given a higher purity.