Synthesis and Photosensitization Evaluation of Some Novel Polyheterocyclic Cyanine Dyes

Abstract

New polyheterocyclic compound, namely 4-methyl-6-oxo-2-phenyl-furo [(3,2-d)pyrazole; (  3 ,  2 -d) imidazole] was prepared and oriented to synthesis of some novel monomethine cyanine dyes, dimethine cyanine dyes and mono/di-mixed methine cyanine dyes. The electronic visible absorption spectra of all the synthesized cyanine dyes were investigated in 95% ethanol solution to evaluate their photosensitization properties. Structural identification was carried out via the elemental analysis, visible spectra, mass spectrometry, IR and 1 H NMR spectroscopic data.Keywords: cyanine dyes, synthesis, photosensitization, monomethine cyanine dyes, dimethine cyanine dyes, mixed methine cyanine dyes. IntroductionCyanine dyes [1][2][3][4][5][6][7][8][9][10][11][12][13][14] are a class of organic heterocyclic dyes, which have long captured the interest of the scientific community. This is because the class of cyanine dyes has proved to be particularly useful in a diverse and a broad area of science, technology and engineering. Their uses and applications includes but not limited to color and non color (black and white) photography, in high energy laser and digital image storage, analytical reagents over a wide range of pH of media, indicators for solvent polarity, in biological and biomedical use as molecular probes and as fluorescent dyes commonly used for DNA visualization assays. In addition, cyanine dyes [15][16][17][18][19][20][21][22][23][24][25][26][27][28] are widely used as optical recording materials, thermal writing display, laser printers, laser filters, absorptivity and antimicrobial efficiency, for probing lipophilic environments, halophobic pockets of enzymes and components of supramolecular structures.Taking into account and consideration the above significant benefits of cyanine dyes, in this research paper we prepared new photosensitizers cyanine dyes as new synthesis contribution and spectroscopic investigation in this field and may be used and/or applied in any of the wide mentioned application field of cyanine dyes, particularly as photographic sensitizers in photosensitive material industry, as probes for determining solvent polarity in solution chemistry, and/or as indicators in operations of acid/base titrations.

Novel Polyheterocyclic Cyanine Dyes: Synthesis, Photosensitiztion and Solvent/Electronic Transitions Correlation

“…The cyanine dyes were thought to be better photosensitizers when they absorb the visible light to initiate the electronic transitions at higher wavelength bands (bathochromic shifted and/or red shifted dyes). Consequently, the photosensitization of the cyanine dyes decreases when they absorb the visible light to initiate the electronic transitions at lower wavelength bands (hypsochromic shifted and/or blue shifted dyes) (Shindy et al, 2002;Shindy et al, 2006;Shindy et al, 2015a;Shindy et al, 2015b). So, we may say that the photosensitization of one cyanine dye is higher than the other one if the wavelength of the maximum absorption spectrum of the former one is longer than that of the latter one.…”

“…Cyanine dyes Shindy, 2016;Shindy, 2018;Shindy et al, 2017a;Solomon et al, 2014;Lynch et al, 2013;Shindy et al, 2012;Arjona et al, 2016;Shindy et al, 2015;Shindy, 2015;Shindy, Koraiem, 2008) have a wide range and various applications in different fields of science and technology. Their uses and applications include but not limited to spectral sensitizers for silver halide emulsions in photographic material industry for coloured and non coloured (black and white) films (cyanine dyes were originally used, and still are, to increase the sensitivity range of photographic emulsions, i. e. to increase the range of wavelengths which will form an image on the film) (Msaki,…”

“…Cyanine dyes Shindy, 2016;Shindy, 2018;Shindy et al, 2017a;Solomon et al, 2014;Lynch et al, 2013;Shindy et al, 2012;Arjona et al, 2016;Shindy et al, 2015;Shindy, 2015;Shindy, Koraiem, 2008) have a wide range and various applications in different fields of science and technology. Their uses and applications include but not limited to spectral sensitizers for silver halide emulsions in photographic material industry for coloured and non coloured (black and white) films (cyanine dyes were originally used, and still are, to increase the sensitivity range of photographic emulsions, i. e. to increase the range of wavelengths which will form an image on the film) (Msaki, Tadashi, 1992;Mari, 1993;Tadashi, 1992;Nobuaki, 1995;Yoshio, Tadahire, 1999), as tools for lasers (Toshiyoshi et al, 2003;Tsutomu et al, 1994), as optical recording media (Toshio, 1992), optical filters (Hiroshi, 1999), optical information recording disk (Katsuji, Katsuhiko, 1991), as inks containing near-IR absorber for optically readable printing (Rivera et al, 2007), and for the development of integrated optochemical sensors (Clegg et al, 1992).…”

Synthesis and Studies on New Dimethine and Tetramethine Cyanine Dyes

“…al., 2012;Zhang et al, 2008;Deligeorgiev et al, 2007;Keisar et al, 2014;Soriano et al, 2016;Takasu et al, 2006;Zhao et al, 2013;Shindy et al, 2016a;Shershof et al, 2013;Wang, Kim 2009;Komljenovic et al, 2016). This is because the multiplicity uses and applications of cyanine dyes in a diverse and a broad area (Liu et al, 2011;Owens et al, 2014;Matsuoka, 1990;Ansari et al, 2014;Shindy, 2014;Shindy et al, 2014a;Shindy, 2015a;Shindy, 2016;Zhang et al, 2016;Chen et al, 2016).…”

Cytotoxicity and Antimicrobial Activity of Pivalic and Benzoic Acid-Complexed Cu and Mn Complexes

“…In a continuing endeavor to improve biological activity of imidazole and its complexes and for important of ecofriendly synthesis methods [26][27][28][29][30][31][32][33][34][35][36][37][38][39][40], the present study was aimed at synthesizing complexes of imidazole with copper and manganese. The synthesized complexes were characterized by FT-IR spectroscopy along with physical characteristics.…”