Novel Fluorescent Azacyanine Compounds: Improved Synthesis and Optical Properties

Date

2020-09-01

Author

Doğan, Kübra
Forough, M
Persil Çetinkol, Özgül

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

153
views

0
downloads

Benzothiazoles are known to possess a number of biological activities and therefore are considered to be an important scaffold in the design and synthesis of pharmacophores. In this study, an improved synthesis method for novel fluorescent benzothiazole-based cyclic azacyanine (CAC) dyes bearing different electron-donating/withdrawing groups on their scaffold is presented. The improved method enabled us to increase the synthesis yield for the previously reported CACs. More importantly, it allowed us to synthesize new CAC dyes that were not synthesizable with the previously reported method. The synthesized dyes were characterized by H-1 and C-13 NMR spectroscopy, elemental analysis, and mass spectrometry and their optical (absorption and fluorescence) properties were investigated. All of the synthesized CACs were found to be displaying strong absorption within the range of 387-407 nm. The spectral shifts observed in the absorption and fluorescence measurements suggested that the spectroscopic and optical properties of CACs can be directly modulated by the nature of the electron-donating/withdrawing substituents. The fluorescence quantum yields (QYs) of the unsubstituted (parent CAC) and substituted CACs were also measured and compared. The fluorescence QY of CACs with electron-donating substituents (methoxy or ethoxy) was found to be at least four times higher than that of the parent CAC with no substitutions.

Subject Keywords

Binding, Ligands, Spectra, Reveals, Standards, Benzothiazole, Resonance, Derivatives, Cyanine dyes, Photoluminescence quantum yield

URI

https://hdl.handle.net/11511/57205

Journal

ACS OMEGA

DOI

https://doi.org/10.1021/acsomega.0c02202

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Novel Pt(II) complexes containing pyrrole oxime, synthesis, characterization and DNA binding studies Altunöz Erdoğan, Deniz; Ozalp-Yaman, Seniz (Elsevier BV, 2014-05-05) Since the discovery of anticancer activity and subsequent clinical success of cisplatin (cis-[PtCl2(NH3)(2)]), platinum-based compounds have since been widely synthesized and studied as potential chemotherapeutic agents. In this sense, three novel nuclease active Pt(II) complexes with general formula; [Pt(NH3)CI(L)] (1), [Pt(L)(2)] (2), and K[PtCl2(L)] (3) in which L is 1-H-pyrrole-2-carbaldehyde oxime were synthesized. Characterization of complexes was performed by elemental analysis, FT-IR, H-1 NMR and ma...
Design and synthesis of benzene-fused heterocycles: aminopyridazinones, chromenopyridinones and benzopyrazoloxazepines / Keskin, Selbi; Balcı, Metin; Department of Chemistry (2015) The interest in the synthesis of heterocyclic compounds has increased day by day due to their biological activities. This study focuses on the synthesis of different benzene-fused heterocycles. In the first part, we synthesized novel class of compounds, 4-aminophthalazin-1(2H)-ones starting from methyl 2-(2-methoxy-2-oxoethyl)-benzoate. Methylene group in this starting material was oxidized to the corresponding ketoester. Reaction of ketoesters with hydrazine derivatives provided the hydrazone derivatives. ...
Development of new methods for the synthesis of five-, six-and seven-membered heterocyclic compounds Karadeniz, Eda; Zora, Metin; Department of Chemistry (2019) Synthesis of heterocyclic compounds has become an important area among organic chemists since they occupy a unique position in the design and synthesis of novel biologically active agents that exhibit noteworthy medicinal activities. In this regard, N-propargylic β-enaminones have been recognized as valuable substrates in synthesis because they afford a variety of heterocyclic compounds upon treatment with proper reagents. In this study, new reactivity patterns of N-propargylic β-enaminones were investigate...
Amber-Compatible Parametrization Procedure for Peptide-like Compounds: Application to 1,4-and 1,5-Substituted Triazole-Based Peptidomimetics Marıon, Antoıne; Kracker, Oliver; Froehr, Tanja; Latajka, Rafal; Sewald, Norbert; Antes, Iris (American Chemical Society (ACS), 2018-01-01) Peptidomimetics are molecules of particular interest in the context of drug design and development. They are proteolytically and metabolically more stable than their natural peptide counterparts but still offer high specificity toward their biological targets. In recent years, 1,4- and 1,5-disubstituted 1,2,3-triazole-based peptidomimetics have emerged as promising lead compounds for the design of various inhibitory and tumor-targeting molecules as well as for the synthesis of peptide analogues. The growing...
Development of new methods for the synthesis of pyrazoles, 4-iodopyrazoles, isoxazoles and 1,2,4-oxadiazoles Kıvrak, Arif; Zora, Metin; Department of Chemistry (2011) Synthesis of five-membered heteroaromatic compounds such as pyrazoles, isoxazoles and 1,2,4-oxadiazoles are important for pharmaceutical industry and material science due to their applications. Although there are many methods to prepare such compounds, new variants continue to appear since they exhibit a wide range of biological and medicinal activities. In this thesis, new methods were developed for the synthesis of 4-iodopyrazoles, pyrazoles, isoxazoles, 1,2,4-oxadiazoles and/or 1,2,4-oxadiazepines. In th...

Citation Formats

K. Doğan, M. Forough, and Ö. Persil Çetinkol, “Novel Fluorescent Azacyanine Compounds: Improved Synthesis and Optical Properties,” ACS OMEGA, pp. 22874–22882, 2020, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57205.