Squaraines based on 2-arylpyrroles

Bonnett, Raymond; Motevalli, Majid; Siu, Jason

doi:10.1016/j.tet.2004.07.023

Cited by 25 publications

(15 citation statements)

References 34 publications

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“…A number of different squaraines are currently considered as potential second generation photosensitizers for PDT, mainly as a consequence of their intense absorption and emission localized in the transparency window of biological tissue (600-900 nm). Amongst the different employed structural motifs are: heteoaryl anhydrobases, [16,63] aniline, [12] pyrrole, [19,34] indolizine, [24,34] quinoline, [26] and trihydroxybenzene derivatives. [15] Despite the huge synthetic effort so far reported, only a few of these dyes have been further investigated in vitro on tumour cells or in real PDT trials on small animals.…”

Section: Photo Dynamic Therapy (Pdt)mentioning

confidence: 99%

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Squaraine Compounds: Tailored Design and Synthesis towards a Variety of Material Science Applications

2010

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The interest in squaraine compounds, a relatively old class of dyes, has been recently renewed due to their potential usefulness in a large number of technologically relevant fields such as two-photon absorbing materials, field-effect transistors, solar cells, NIR-emitting fluorescent probes and sensitizers for photodynamic therapy. Aim of the present review is to summarize the most convenient strategies for squaraines and polysquaraines syntheses and to discuss the design strategies enabling for the preparation of squaraines having properties relevant for a given material application. In particular, in the first section of the review we will describe the various synthetic approaches for the preparation of squaraine and polysquaraine derivatives. The second section will

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Section: Photo Dynamic Therapy (Pdt)mentioning

confidence: 99%

“…Bonnet synthesized a number of squaraines based on 2-arylpyrroles like derivatives 2-4. [19] It is worthwhile to comment on the isolated yields, the more pronounced is the electron-rich character of the activated arene, the higher is the yield in the corresponding squaraine (Scheme 4, a).…”

Section: Symmetric Derivativesmentioning

confidence: 99%

Squaraine Compounds: Tailored Design and Synthesis towards a Variety of Material Science Applications

2010

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“…18,19 The band at ca 590 nm in the PDPS spectrum and at ca 680 nm in the PMPS can be associated with bands observed at 560-600 nm in electronic spectra of several squaraines. 8,20,21 The FTIR spectra of the polysquaraines, squaric acid and potassium squarate are presented in Fig. 4.…”

Section: Resultsmentioning

confidence: 99%

Vibrational characterization of poly(1‐methylpyrrole‐ co‐squaric acid) and poly(1‐dodecylpyrrole‐co‐squaric acid) by enhanced Raman spectroscopy

Sant’Ana

Siqueira

Santos

et al. 2006

J Raman Spectroscopy

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Poly(1-methylpyrrole-co-squaric acid) (PMPS) and poly(1-dodecylpyrrole-co-squaric acid) (PDPS), copolymers of the class of polysquaraines, were synthesized and their structure determined by UV-VIS-NIR, resonance Raman and surface-enhanced Raman scattering (SERS) and electron paramagnetic resonance (EPR) spectroscopies. The spectroscopic results led to a structure different from that proposed in the literature, having radical units localized in the protonated squarate moieties and polypyrrole dication-like segments. The resonance Raman profiles indicate the presence of two chromospheres that are consistent with the electronic data. The Raman assignment was supported by density functional theory (DFT) calculations.

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“…The properties of squarylium dye molecules have been extensively studied by Liang et al [13]. Typically, they exhibit a characteristically intense absorption band in the range of 640-850 nm [14]. Nakazumi et al [15], showed that squarylium dyes experience enhanced fluorescence emission upon binding to BSA and HSA.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Mono- and Bis-Squarylium Dyes as Pre-Column and On-Column Labels for Protein Analysis by Capillary Electrophoresis with Laser-Induced Fluorescence Detection

Lin¹,

Rockett²

2012

J Anal Bioanal Tech

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Labeling proteins with fluorescent dyes offers a powerful tool for monitoring protein interactions in vitro and in vivo. In order for this tool to be effective, the nature of the dyes -absorbance and emission properties, solution stability, pH range, and mechanisms for protein interaction -must first be considered. Two new asymmetric, squarylium dyes, bis-SQHN-4d and SQHN-3c, were shown to be only weakly fluorescent in aqueous buffers in the absence of proteins. However, their spectra showed a dramatic increase in fluorescence intensity upon the addition of Human Serum Albumin (HSA) or Bovine Serum Albumin (BSA) as model proteins. The enhanced fluorescence properties, attributed to noncovalent binding, allowed the use of the new squarylium dyes as probes for the low-level detection of proteins in a mixture (including myoglobin (pI=7.16), transferrin (pI=5.9), and HSA (pI=4.8)), separated by Capillary Electrophoresis with Laser-Induced Fluorescence detection (CE-LIF). Because of the low background fluorescence of these probes, on-column labeling was feasible and led to simple and rapid protein detection. This labeling protocol offered greater sensitivity than the more conventional pre-column labeling protocol (with a 10-fold lower limit of detection for HSA with bis-SQHN-4d). A limit of detection for HSA (by CE-LIF with on-column labeling with bis-SQHN-4d) of 3.42 x 10 -8 M indicates that this dye is well suited to the development of other protein assays. Citation: Lin X, Rockett S, Massie TL, Turner GB, Asymmetric Mono-and Bis-Squarylium Dyes as Pre-Column and OnColumn Labels for Protein Analysis by Capillary Electrophoresis with Laser-Induced Fluorescence Detection. J Anal Bioanal Techniques S9:001.

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Squaraines based on 2-arylpyrroles

Cited by 25 publications

References 34 publications

Squaraine Compounds: Tailored Design and Synthesis towards a Variety of Material Science Applications

Squaraine Compounds: Tailored Design and Synthesis towards a Variety of Material Science Applications

Vibrational characterization of poly(1‐methylpyrrole‐ co‐squaric acid) and poly(1‐dodecylpyrrole‐co‐squaric acid) by enhanced Raman spectroscopy

Asymmetric Mono- and Bis-Squarylium Dyes as Pre-Column and On-Column Labels for Protein Analysis by Capillary Electrophoresis with Laser-Induced Fluorescence Detection

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