Abstract
Hemicyanine dyes are a subclass of polymethine colorants. At one end of their polymethine chain is an unsaturated heterocyclic ring possessing a nitrogen atom as would be found in a cyanine dye. However, the other end is terminated by a nitrogen atom that does not form part of an unsaturated heterocycle. The name alludes to their half-cyanine substitution pattern. Later the scope of the term “hemicyanine” was extended to the phenylogous dyes where there is a phenyl group between the two terminal nitrogen atoms. The first main technical application of hemicyanine dyes was in textile coloration. Nowadays hemicyanine dyes are used extensively as optical probes of cell membrane potential.
References
1. Hamer FM. The cyanine dyes and related compounds. In: Weissberger A, editor. The chemistry of heterocyclic compounds. vol. 18. New York: Interscience, 1964.10.1002/9780470186794Search in Google Scholar
2. Griffiths J. Colour and constitution of organic molecules. London: Academic Press, 1976.Search in Google Scholar
3. Sturmer DM. Syntheses and properties of cyanine and related dyes. In: Weissberger A, Taylor EC, editors. The chemistry of heterocyclic compounds. vol. 30. New York: Wiley, 1977:441–587.10.1002/9780470187005.ch8Search in Google Scholar
4. Mishra A, Behera RK, Behera PK, Mishra BK, Behera GB. Cyanine dyes during the 1990s: a review. Chem Rev. 2000;100:1973.10.1021/cr990402tSearch in Google Scholar
5. Mustroph H. Cyanine dyes. Phys Sci Rev. 2020;5. DOI:10.1515/psr-2020-0145.Search in Google Scholar
6. White FL, Keyes GH. US 2 263 749. 23 Apr 1937.10.1136/bmj.2.4006.749Search in Google Scholar
7. Picus N, Spoerri PE. Bridge substituted hemicyanines. J Am Chem Soc. 1948;70:3073.10.1021/ja01189a069Search in Google Scholar
8. Berneth H. Methine dyes and pigments. In: Elvers B, editor. Ullmann’s encyclopedia of industrial chemistry. Weinheim: Wiley-VCH, 2012.Search in Google Scholar
9. Hübener G, Lambacher A, Fromherz P. Anellated hemicyanine dyes with large symmetrical solvatochromism of absorption and fluorescence. J Phys Chem B. 2003;107:7896.10.1021/jp0345809Search in Google Scholar
10. König W. Über den Begriff der „Polymethinfarbstoffe“ und eine davon ableitbare allgemeine Farbstoff-Formel als Grundlage einer neuen Systematik der Farbenchemie. J Prakt Chem. [2] 1926; 112: 1.10.1002/prac.19261120101Search in Google Scholar
11. Sturmer DM, Diehl DR. Polymethine dyes. In: Kirk-Othmer encyclopedia of chemical technology, 3rd ed. vol. 18, Wiley, New York, 1982:848–74.Search in Google Scholar
12. Tyutyulkov N, Fabian J, Mehlhorn A, Dietz F, Tadjer A. Polymethine dyes – structure and properties. Sofia: St. Kliment Ohridski University Press, 1991.Search in Google Scholar
13. Mustroph H. Polymethine dyes. Phys Sci Rev. 2020;5. DOI:10.1515/psr-2019-0084.Search in Google Scholar
14. Mustroph H. Dyes: quantum chemical calculation of electronic spectra. Phys Sci Rev. 2019;4. DOI:10.1515/psr-2019–0040.Search in Google Scholar
15. Mustroph H, Ernst S, Senns B, Towns AD. Molecular electronic spectroscopy: from often neglected fundamental principles to limitations of state-of-the-art computational methods. Color Technol. 2015;131:9.10.1111/cote.12120Search in Google Scholar
16. Mustroph H, Towns A. Fine structure in electronic spectra of cyanine dyes: are sub-bands largely determined by a dominant vibration or a collection of singly-excited vibrations? Chem Phys Chem. 2018;19:1016.10.1002/cphc.201701300Search in Google Scholar
17. Schmidt H, Wizinger R. Über die Vinylenhomologen der Di- und Triphenylmethanfarbstoffe. III. Liebigs Ann Chem. 1959;623:204.10.1002/jlac.19596230123Search in Google Scholar
18. Tolbert LM, Zhao X. Beyond the cyanine limit: Peierls distortion and symmetry collapse in a polymethine dye. J Am Chem Soc. 1997;119:3253.10.1021/ja9626953Search in Google Scholar
19. Grinvald A, Hildesheim R, Farber IC, Anglister L. Improved fluorescent probes for the measurement of rapid changes in membrane potential. Biophys J. 1982;39:301.10.1016/S0006-3495(82)84520-7Search in Google Scholar
20. Brooker LG, Keyes GH, Sprague RH, VanDyke RH, VanLare E, VanZandt G, et al. Color and constitution. X. Absorption of the merocyanines. J Am Chem Soc. 1951;73:5332.10.1021/ja01155a095Search in Google Scholar
21. Mustroph H, Reiner K, Senns B, Mistol J, Ernst S, Keil D, et al. 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. 2012;18:8140.10.1002/chem.201101830Search in Google Scholar
22. Brooker LG, Sklar AL, Cressman HW, Keyes GH, Smith LH, Sprague RH, et al. Color and constitution. VII. Interpretation of absorption of dyes containing heterocyclic nuclei of different basicities. J Am Chem Soc. 1875;67:1945.10.1021/ja01227a002Search in Google Scholar
23. Mustroph H, Reiner K, Senns B. Bond length alternation in unsymmetrical cyanine dyes and its influence on the vibrational structure of their electronic absorption spectra. Color Technol. 2017;133:469.10.1111/cote.12303Search in Google Scholar
24. Mikhailenko FA, Shevchuk LI, Rozhdestvenskaya IT. Mono- and dimethine dyes from 2-dimethylamino-5-formylfurans, -thiophenes, and -selenophenes. Khim Geterotsikl Soedin. 1975:316.10.1002/chin.197527447Search in Google Scholar
25. König W. Zur Frage der Konstitution der Cyaninfarbstoffe. J Prakt Chem. [2] 1912;86: 166.10.1002/prac.19120860110Search in Google Scholar
26. Mills WH, Pope WJ. 2-p-dimethylaminostyrylpyridine methiodide, a new photographic sensitizer. J Chem Soc Trans. 1922;121:946.10.1039/CT9222100946Search in Google Scholar
27. König E. DE 395 666. 23 May 1922.Search in Google Scholar
28. James TH, editor. The theory of the photographic process. 4th ed. New York: Macmillan, 1977.Search in Google Scholar
29. Keller K, Kampfer H, Matejec R, Lapp O, Krafft W, Frenken H, et al. Photography. In: Elvers B, editor. Ullmann’s encyclopedia of industrial chemistry. Weinheim: Wiley-VCH, 2000.10.1002/14356007.a20_001Search in Google Scholar
30. Fujita S. Organic chemistry in photography. Berlin: Springer, 2004.10.1007/978-3-662-09130-2Search in Google Scholar
31. Hunger K, editor. Industrial dyes, chemistry, properties, applications. Weinheim: Wiley-VCH, 2003.10.1002/3527602011Search in Google Scholar
32. Waggoner AS. Dye indicators of membrane potential. Annu Rev Biophys Bioeng. 1979;8:47.10.1146/annurev.bb.08.060179.000403Search in Google Scholar
33. Loew LM, Bonneville GW, Surow J. Charge shift optical probes of membrane potential. Theory Bio Chem. 1978;17:4065.10.1021/bi00612a030Search in Google Scholar
34. Loew LM, Simpson LL. Charge-shift probes of membrane potential: a probable electrochromic mechanism for p-aminostyrylpyridinium probes on a hemispherical lipid bilayer. Biophys J. 1981;34:353.10.1016/S0006-3495(81)84854-0Search in Google Scholar
35. Fluhler E, Burnham VG, Loew LM. Spectra, membrane binding, and potentiometric response of new charge response of new charge shift probes. Bio Chem. 1985;24:5749.10.1021/bi00342a010Search in Google Scholar
36. Fromherz P, Hübener G, Kuhn B, Hinner MJ. ANNINE-6plus, a voltage-sensitive dye with good solubility, strong membrane binding and high sensitivity. Eur Biophys J. 2008;37:509.10.1007/s00249-007-0210-ySearch in Google Scholar
37. Kabatc J, Jurek K. Synthesis, properties, and application of new benzothiazole-based sensitisers in polymer chemistry. Color Technol. 2015;131:183.10.1111/cote.12149Search in Google Scholar
38. Lalevée J, Fouassier J-P, editors. Polymer chemistry series. Photopolymerisation initiating systems, vol. 29. London: RSC, 2018.10.1039/9781788013307Search in Google Scholar
39. Deligeorgiev T, Gadjev N, Kaloyanova S, Lesev N, Vasilev A, Alexiev A. A novel general method for fast and easy preparation of cationic, neutral dimethinehemicyanine and dimethine dyes by uncatalysed Knoevenagel condensation. Color Technol. 2012;128:417.10.1111/j.1478-4408.2012.00408.xSearch in Google Scholar
© 2020 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Reviews
- Influence of lime (CaO) on low temperature leaching of some types of bauxite from Guinea
- Ethnobotanical survey, phytoconstituents and antibacterial investigation of Rapanea melanophloeos (L.) Mez. bark, fruit and leaf extracts
- Catalytic properties of supramolecular polymetallated porphyrins
- Lignin-based polymers
- Bio-based polyhydroxyalkanoates blends and composites
- Biodegradable poly(butylene adipate-co-terephthalate) (PBAT)
- Repurposing tires – alternate energy source?
- Theoretical investigation of the stability, reactivity, and the interaction of methyl-substituted peridinium-based ionic liquids
- Polymeric membranes for biomedical applications
- Design of locally sourced activated charcoal filter from maize cob for wastewater decontamination: an approach to fight waste with waste
- Synthesis of biologically active heterocyclic compounds from allenic and acetylenic nitriles and related compounds
- Magnetic measurement methods to probe nanoparticle–matrix interactions
- Health and exposure risk assessment of heavy metals in rainwater samples from selected locations in Rivers State, Nigeria
- Evaluation of raw, treated and effluent water quality from selected water treatment plants: a case study of Lagos Water Corporation
- A chemoinformatic analysis of atoms, scaffolds and functional groups in natural products
- Hemicyanine dyes
- Thermodynamics of the micellization of quaternary based cationic surfactants in triethanolamine-water media: a conductometry study
- Compounds isolated from hexane fraction of Alternanthera brasiliensis show synergistic activity against methicillin resistant Staphylococcus aureus
- Internal structures and mechanical properties of magnetic gels and suspensions
- SPIONs and magnetic hybrid materials: Synthesis, toxicology and biomedical applications
- Magnetic field controlled behavior of magnetic gels studied using particle-based simulations
- The microstructure of magnetorheological materials characterized by means of computed X-ray microtomography
- Core-modified porphyrins: novel building blocks in chemistry
- Anticancer potential of indole derivatives: an update
- Novel drug design and bioinformatics: an introduction
- Multi-objective optimization of CCUS supply chains for European countries with higher carbon dioxide emissions
- Exergy analysis of an atmospheric residue desulphurization hydrotreating process for a crude oil refinery
- Development in nanomembrane-based filtration of emerging contaminants
- Supply chain optimization framework for CO2 capture, utilization, and storage in Germany
- Naturally occurring heterocyclic anticancer compounds
- Part-II- in silico drug design: application and success
- Advances in biopolymer composites and biomaterials for the removal of emerging contaminants
- Nanobiocatalysts and photocatalyst in dye degradation
- 3D tumor model – a platform for anticancer drug development
- Hydrogen production via water splitting over graphitic carbon nitride (g-C3N4 )-based photocatalysis
Articles in the same Issue
- Frontmatter
- Reviews
- Influence of lime (CaO) on low temperature leaching of some types of bauxite from Guinea
- Ethnobotanical survey, phytoconstituents and antibacterial investigation of Rapanea melanophloeos (L.) Mez. bark, fruit and leaf extracts
- Catalytic properties of supramolecular polymetallated porphyrins
- Lignin-based polymers
- Bio-based polyhydroxyalkanoates blends and composites
- Biodegradable poly(butylene adipate-co-terephthalate) (PBAT)
- Repurposing tires – alternate energy source?
- Theoretical investigation of the stability, reactivity, and the interaction of methyl-substituted peridinium-based ionic liquids
- Polymeric membranes for biomedical applications
- Design of locally sourced activated charcoal filter from maize cob for wastewater decontamination: an approach to fight waste with waste
- Synthesis of biologically active heterocyclic compounds from allenic and acetylenic nitriles and related compounds
- Magnetic measurement methods to probe nanoparticle–matrix interactions
- Health and exposure risk assessment of heavy metals in rainwater samples from selected locations in Rivers State, Nigeria
- Evaluation of raw, treated and effluent water quality from selected water treatment plants: a case study of Lagos Water Corporation
- A chemoinformatic analysis of atoms, scaffolds and functional groups in natural products
- Hemicyanine dyes
- Thermodynamics of the micellization of quaternary based cationic surfactants in triethanolamine-water media: a conductometry study
- Compounds isolated from hexane fraction of Alternanthera brasiliensis show synergistic activity against methicillin resistant Staphylococcus aureus
- Internal structures and mechanical properties of magnetic gels and suspensions
- SPIONs and magnetic hybrid materials: Synthesis, toxicology and biomedical applications
- Magnetic field controlled behavior of magnetic gels studied using particle-based simulations
- The microstructure of magnetorheological materials characterized by means of computed X-ray microtomography
- Core-modified porphyrins: novel building blocks in chemistry
- Anticancer potential of indole derivatives: an update
- Novel drug design and bioinformatics: an introduction
- Multi-objective optimization of CCUS supply chains for European countries with higher carbon dioxide emissions
- Exergy analysis of an atmospheric residue desulphurization hydrotreating process for a crude oil refinery
- Development in nanomembrane-based filtration of emerging contaminants
- Supply chain optimization framework for CO2 capture, utilization, and storage in Germany
- Naturally occurring heterocyclic anticancer compounds
- Part-II- in silico drug design: application and success
- Advances in biopolymer composites and biomaterials for the removal of emerging contaminants
- Nanobiocatalysts and photocatalyst in dye degradation
- 3D tumor model – a platform for anticancer drug development
- Hydrogen production via water splitting over graphitic carbon nitride (g-C3N4 )-based photocatalysis