Rigidized monomethine cyanines

Details Rigidized monomethine cyanines Rigidized monomethine cyanines

1995-06-07

1998-12-22

Dees, Jose' G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548110, 568 6, C07D49816

Patent

active

058521917

ABSTRACT:
Boron complexes of certain bis-heterocyclic compounds are provided. The complexes resemble monomethine cyanines and are useful for imparting fluorescent properties to materials by covalent and noncovalent association. The compounds have the following general formula: ##STR1## wherein the dotted lines Z.sub.1 and Z.sub.2 represent the atoms necessary to complete a structure selected from the group consisting of one ring, two fused rings, and three fused rings, each said ring having five or six atoms, and each said ring comprising carbon atoms and, optionally, no more than two atoms selected from oxygen, nitrogen and sulfur, and R.sub.1 through R.sub.5 represent various atoms or groups and M is Cl or F.

REFERENCES:
patent: 2432080 (1947-12-01), Anish
patent: 2541400 (1951-02-01), Brooker et al.
patent: 3148187 (1964-09-01), Heseltine
patent: 3250780 (1966-05-01), Rai et al.
patent: 3729467 (1973-04-01), Zweldler et al.
patent: 4064136 (1977-12-01), Lowe et al.
patent: 4337063 (1982-06-01), Mihara et al.
patent: 4404289 (1983-09-01), Masuda et al.
patent: 4405711 (1983-09-01), Masuda et al.
patent: 4774339 (1988-09-01), Haugland et al.
patent: 4916711 (1990-04-01), Bayer et al.
patent: 5187288 (1993-02-01), Kang et al.
patent: 5248782 (1993-09-01), Haugland et al.
patent: 5268486 (1993-12-01), Waggoner et a.
patent: 5274113 (1993-12-01), Kang et al.
patent: 5338854 (1994-08-01), Kang et al.
patent: 5433896 (1995-07-01), Kang et al.
patent: 5446157 (1995-08-01), Morgan et al.
patent: 5451663 (1995-09-01), Kang et al.
D.M. Sturmer and W.S. Gaugh, "Spectral Sensitization by Sterically Hindered Chromophores", Photographic Science and Engineering, vol. 19, No. 5 (Sep.-Oct. 1975), pp. 273-278.
T. Ramos et al., "Crystal and molecular structure of 6-phenyl-13H-pyrimido and Spectroscopic Research, vol. 21, No. 2 (Apr. 1991), pp. 179-182.
G. Scheibe et al., "Das Franck-condon-Prinzip und die Lichtabsorpotion von Merocyaninen", Z. physik, Chem. Neue Folge, Bd. 64, S. 97-114 (1969).
van Koeveringe et al., Novel pyrromethenes 1-Oxygen and 1-sulfur analogues; evidence for photochemical Z-E isomerization, Recl. Trav. Chim. Pas-Bas, vol. 96, p. 55 (1977).
Lapworth et al., Oxidation Products of Oleic Acid. Part I. Conversion of Oleic Acid into Dihydroxystearic Acid and the Determination of the Higher Saturated Acids in Mixed Acids from Natural Sources, J. Chem. Soc., 1628 (1925).
Saito, et al., Combination of Borane-Dimethyl Sulfide Complex With Catalytic Sodium Tetrahydroborate as a Selective Reducing Agent For a-Hydroxy Esters, Versatile Chiral Building Block from (s)-(-) Malic Acid, Chem. Letters, 1389-1392 (1984).
Newkome, et al., Nitrile-Stabilized Carbanions. Nucleophilic Substitution Reactions on Bromopyridines, J. Org. Chem., 1988, 53, 786-780.
Saito, et al., Synthetic Studies Using a .beta.-Unsaturated Nitriles: A Convenient Preparation of 1,3-Bezothiazole Derivatives, Synthesis, (3), pp. 210-211 (1983).
McElvain, et al., Orthoesters and Related Compounds from Malono-and Succinonitriles, JACS, vol. 71, pp. 40-46 (1949).
Ramos, et al., Tautomerism of Bis(2-Benzothiazolyl)Arylmethanes, Heterocycles, vol. 29, No. 1, pp. 165-180 (1989).
Avendano et al., Tautomerism of bis(2-benzothiazolyl)methanes, Can. J. Chem., vol. 67, pp. 1467-1473 (1988).
Vos de Wael, et al., Pyrromethene-BF.sub.2 complexes (4,4'-difluoro-4-bora-3a,4a-diaza-s-indacenes). Synthesis and luminescence properties, Recl. Trav. Chim. Pay-Bas, vol. 96, p. 306 (1977).
Wories, et a., A novel water-soluble fluorescent probe: Synthesis, luminescence and biological properties of the sodium salt of the 4-sulfonato-3,3',5,5'-tetramethyl-2,2'-pyrromethen-1,1'BF.sub.2 Complex, Recl. Trav. Chim. Pays-Bas 104, 288-291 (1985).
Treibs, et al., Difluorboryl-Komplexe von Di- und Tripyrrylmethen, Liebigs Ann. Chem., vol. 718, pp. 208-223 (1968).
Bodipy: The New Fluorescein Substitute, Bioprobes, No. 10, (Molecular Probes, Inc., Eugene, Or.) (Dec. 1989).
Haugland, Handbook of Fluorescent Probes and Research Chemicals, (5th ed. 1992) Molecular Probes, Inc., Eugene, OR, pp. 9-110, 159-180, 203-274.
Reactive Bodipy Dyes, (Molecular Probes, Inc., Eugene, OR 1992), pp. 1-3.
Shah et al., Pyrromethene-BF.sub.2 Complexes as Laser Dyes:1., Heteroatom Chemistry (vol. 1, No. 5, 1990).
Kaplan et al., "Synthesis and Luminescence--Spectral Characteristics of the Chelates of Boron with Diheterylamines" (1991) translated from Zhurnal Organicheskai Khimii, vol. 27, No. 4, pp. 872-877, Apr. 1991.
Kang and Haugland, "Spectral Properties of 4-Sulfornato-3, 3',5'5'--Tetramethyl-22'-Pyrromethen-1,1'--Barandifluoride Complex (Bodipy), Its Sodium Salt, and Protein Derivatives," SPIE, vol. 1063 New Technologies in Cytometry (1989), pp. 68-73.
Douglass et al., "Diazobarayclic Cations. III. A Homomorph of 9, 10-Dihydroanthracene (1)." Journal of Heterocyclic Chemistry (vol. 10, 1973), pp. 255-257.
Scheibe and Daltrozzo, Advances in Heterocyclic Chemistry, vol. 6, pp. 153-181 (Academic Press 1965).
Ramos et al., "Crystal and Molecular Structure of 6-Phenyl-13H-Pyrimido and Spectroscopic Research, vol. 21, No. 2, 1991, pp. 179-182.
Abbotto, "Novel Heteroaromatic and Heteroalicyclic Metal Methanates, -Thiazolinyl)!}", Gazzettia Chimica Italiana, 121, 1991, pp. 303-305.
Hugel, A Facile Synthesis of (.+-.)2-(4-Chlorophenyl)-a-Methyl-5-Benzoxazoleacetic Acid (Benoxaprofen) Comm. 15, pp. 1075-1080 (1985).
Muller et al., 21.C.sub.2 -Symmetric 4,4',5,5'-Tetrahydrobi(oxazoles) and Enantioselective Catalysis, Hel. Chim. Acta, 74, 232-240 (1991).
Hamer, The Cyanine Dyes and Related Compounds (John Wiley & Sons, New York 1964), pp. 32-85.
Ramos et al., "Reactivity of Aryl-and Heteroarylmalonates against ortho-Dinicleophiles. Triaryl (heteroaryl) methane Synthesis", J. Hetero. Chem. 24, 247 (1987).

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