Synthesis of near-infrared absorbing pyrylium-squaraine dye for selective detection of Hg2+

Rao, B. Appa; Kim, Hyungjoo; Son, Young-Α

doi:10.1016/j.snb.2013.07.073

Cited by 41 publications

(14 citation statements)

References 105 publications

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“…Son and co-workers employed a pyrylium–squaraine platform ( 228 ) as an indicator for detection of Hg 2+ . The sensor displayed two absorption peaks at 641 and 697 nm.…”

Section: Chemosensors Based On Squarainesmentioning

confidence: 99%

Recent Development of Chemosensors Based on Cyanine Platforms

et al. 2016

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The cyanine platforms including cyanine, hemicyanine, and squaraine are good candidates for developing chemosensors because of their excellent photophysical properties, outstanding biocompatibility, and low toxicity to living systems. A huge amount of research work involving chemosensors based on the cyanine platforms has emerged in recent years. This review focuses on the development from 2000 to 2015, in which cyanine, hemicyanine, and squaraine sensors will be separately summarized. In each section, a systematization according to the type of detection mechanism is established. The basic principles about the design of the chemosensors and their applications as bioimaging agents are clearly discussed. In addition, we emphasize the advances that have been made in improving the detection performance through incorporation of the chemosensors into nanoparticles.

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“…Son and co-workers employed a pyrylium–squaraine platform ( 228 ) as an indicator for detection of Hg 2+ . The sensor displayed two absorption peaks at 641 and 697 nm.…”

Section: Chemosensors Based On Squarainesmentioning

confidence: 99%

Recent Development of Chemosensors Based on Cyanine Platforms

et al. 2016

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“…Among the squaric acid derivatives, it is essential to emphasize the squaraine cyanine dyes, a core of functional dyes, first reported by Treibs and Jacob [10], known for its good photochemical stability, conductivity, sharp and intense Vis/NIR absorption and high absorption coefficients [8,11,12]. These photochemical and photophysical properties encourage the study of the suitability of these core of dyes to their application as photoconductive and nonlinear optical materials [13,14], sensitizers for organic solar cells [15,16], fluorescent probes for detection of functional groups [17], toxic substances [18][19][20] or biomolecules [21][22][23], and as photodynamic therapy (PDT) photosensitizers [9,24,25].…”

Section: Introductionmentioning

confidence: 99%

Photophysicochemical Properties and In Vitro Phototherapeutic Effects of Iodoquinoline- and Benzothiazole-Derived Unsymmetrical Squaraine Cyanine Dyes

et al. 2019

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The search to replace conventional cancer treatment therapies, such as chemotherapy, radiotherapy and surgery has led over the last ten years, to a substantial effort in the development of several classes of photodynamic therapy photosensitizers with desired photophysicochemical and photobiological properties.Herein we report the synthesis of 6-iodoquinoline-and benzothiazole-based unsymmetrical squaraine cyanine dyes functionalized with amine groups located in the four-membered central ring. Their photodegradation and singlet oxygen production ability, as well as their in vitro photocytotoxicity against Caco-2 and HepG2 cell lines using a 630.8 ± 0.8 nm centered light-emitting diode system, were also investigated. All photosensitizer candidates displayed strong absorption within the tissue transparency spectral region (650-850 nm). The synthesized dyes were found to have moderate light stability. The potential of these compounds is evidenced by their cytotoxic activity against both tumor cell lines, highlighting the zwitterionic unsubstituted dye, which showed more intense photodynamic activity. Although the singlet oxygen quantum yields of these iodinated derivatives are considered low, it could be concluded that their introduction into the quinoline heterocycle was highly advantageous as it played a role in increasing selective cytotoxicity in the presence of light. Thus, the novel synthesized dyes present photophysicochemical and in vitro photobiological properties that make them excellent photosensitizer candidates for photodynamic therapy.

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“…Squaraines are 1,3-disubstituted squaric acids existing in a zwitter-ionic form which consists of a donor–acceptor–donor (D–A–D) structure due to the strong electron withdrawing central squaryl moiety flanked between aromatic or heterocyclic donor rings on either side. Their planar rigid structure, a strong narrow absorption in the Visible/NIR region, high molar extinction coefficient, intense fluorescence spectra in the red and near-infrared region, good solubility in low polarity solvents, remarkable chemical stability, high redox reversibility, inherent photostability, and good photoconductivity are noteworthy properties of these dyes. − These unique electronic structures and optical properties render them most suitable for a wide range of technological applications such as metal ion sensors, sensitizers in DSSC, photodynamic therapy, electrophotography, long wavelength fluorescent biomedical labels and probes, nonlinear optics, optical data storage, TPA applications, biomedical imaging, xerographic organic photoreceptors, photoconductive material in photocopies, and light emitting field effect transistors …”

Section: Introductionmentioning

confidence: 99%

Greener Protocol for the Synthesis of NIR Fluorescent Indolenine-Based Symmetrical Squaraine Colorants

Khopkar

Deshpande

Shankarling

2018

ACS Sustainable Chem. Eng.

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An environmentally benign synthesis of NIR fluorescent indolenine-based symmetrical squaraines is accomplished by using choline chloride:urea as a biorenewable deep eutectic solvent (DES). This ammonium DES is biodegradable and serves a dual role as a catalyst as well as the reaction medium. Furthermore, DES has been recycled up to four consecutive cycles without significant loss in its activity. The developed method has many advantages compared to those reported in the literature including being environmentally more benign and having operational simplicity, a low reaction temperature, ease of product isolation, a low environmental factor (E-factor), and higher yield for the synthesis of symmetrical squaraine colorants in a short reaction time. In addition, the present method could be implemented on a multigram scale. Thus, it provides a good alternative route for the industrial synthesis of squaraine colorants.

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Synthesis of near-infrared absorbing pyrylium-squaraine dye for selective detection of Hg2+

Cited by 41 publications

References 105 publications

Recent Development of Chemosensors Based on Cyanine Platforms

Recent Development of Chemosensors Based on Cyanine Platforms

Photophysicochemical Properties and In Vitro Phototherapeutic Effects of Iodoquinoline- and Benzothiazole-Derived Unsymmetrical Squaraine Cyanine Dyes

Greener Protocol for the Synthesis of NIR Fluorescent Indolenine-Based Symmetrical Squaraine Colorants

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