New fluorescent monomers and polymers displaying an intramolecular proton-transfer mechanism in the electronically excited state (ESIPT), 1. Synthesis of benzazolylvinylene derivatives and its copolymerization with methyl methacrylate (MMA)

Campo, Leandra Franciscato; Corrêa, Dione Silva; Araújo, Marco Aurélio de; Stéfani, Valter

doi:10.1002/1521-3927(20000801)21:12<832::aid-marc832>3.0.co;2-y

Cited by 40 publications

(20 citation statements)

References 8 publications

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“…The dyes 1a-d were prepared using a previously described methodology. 39 The triazine benzazole derivatives 3a-d were prepared according to Figure 2. In a typical experiment, an equimolar amount of the amino derivative 1a-d and 2,4,6-trichloro-1,3,5-triazine were both dissolved in acetone.…”

Section: Synthesis Of the Triazine Derivativesmentioning

confidence: 99%

Synthesis, characterization and photophysical properties of ESIPT reactive triazine derivatives

Kuplich¹,

Grasel²,

Campo³

et al. 2012

J. Braz. Chem. Soc.

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Uma série de quatro compostos fotoativos derivados da triazina foi obtida a partir da substituição nucleofílica aromática no cloreto cianúrico. Os compostos foram caracterizados por espectroscopia de infravermelho (IR) e ressonância magnética nuclear (NMR de 1 H e 13 C), além de espectrometria de massas de alta resolução (HRMS MALDI). A espectroscopia de absorção na região do UV-Vis e a emissão de fluorescência (no estado sólido e em solução) foram também utilizadas para estudar o comportamento fotofísico destes compostos. Os derivados obtidos são fluorescentes na região do azul-laranja por um mecanismo de transferência protônica intramolecular no estado excitado e apresentam um grande deslocamento de Stokes (6365-10290 cm-1). Os derivados sintetizados neste trabalho reagiram com sucesso com fibras de celulose para dar novos compostos celulósicos fluorescentes. Four new reactive fluorescent triazine derivatives were obtained from nucleophilic aromatic substitution of cyanuric chloride. The compounds were characterized by infrared spectroscopy (IR), nuclear magnetic resonance (13 C and 1 H NMR) and high resolution mass spectrometry (HRMS MALDI). UV-Vis and steady-state fluorescence (in solution and in solid state) spectroscopies were also applied to characterize the photophysical behavior. The dyes are fluorescent by an intramolecular proton transfer mechanism (ESIPT) in the blue-orange region, with a large Stokes shift between 6365-10290 cm-1. The fluorescent cyanuric derivatives could successfully react with cellulose fibers to give new fluorescent cellulosic materials.

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Section: Synthesis Of the Triazine Derivativesmentioning

confidence: 99%

Synthesis, characterization and photophysical properties of ESIPT reactive triazine derivatives

Kuplich¹,

Grasel²,

Campo³

et al. 2012

J. Braz. Chem. Soc.

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“…The HAMBO molecule contains radicals that bind to the benzoxazole nucleus, which in addition to being less susceptible to enzymatic hydrolysis, undergo an excited state intramolecular proton transfer, 26 a mechanism that reduces its chances of being hydrolysed 18 . Thus, the fungistatic effect of HAMBO can be related to a less strong interaction of the benzoxazole nucleus with the microbial cell, producing reversible inhibition.…”

Section: Discussionmentioning

confidence: 99%

In vitro antifungal activity of 2‐(2′‐hydroxy‐5′‐aminophenyl)benzoxazole in Candida spp. strains

Daboit

Stopiglia

Carissimi

et al. 2009

Mycoses

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The development of azole antifungals has allowed for the treatment of several fungal infections. However, the use of these compounds is restricted because of their hepatotoxicity or because they need to be administered together with other drugs in order to prevent resistance to monotherapy. Benzoxazole derivatives are among the most thriving molecular prototypes for the development of antifungal agents. 2-(2'-hydroxyphenyl) benzoxazoles are versatile molecules that emit fluorescence and have antibacterial, antiviral and antifungal properties. 2-(2'-hydroxy-5'-aminophenyl) benzoxazole (HAMBO) was tested against Candida yeast. The inhibition provided by HAMBO was lower than that of fluconazole, showing low antifungal activity against Candida spp., but equivalent to that of benzoxazoles tested in similar studies. HAMBO showed fungistatic activity against all analysed strains. This class of novel benzoxazole compounds may be used as template to produce better antifungal drugs.

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“…Mass spectra were performed on a Hewlett-Packard 1100 MSD mass spectrometer (ESI-MS, APCI-MS) with positive mode. The dyes 1a-b and 2a-b were obtained using the previously described method [32,38]. To a solution of the corresponding amino derivative 1a-b in ethanol (40 ml) was added an equimolar amount of the diethyl (ethoxymethylene)malonate and the ensuing was heated at reflux for 3 h. The precipitate in the reaction mixture was filtered, washed with hot ethanol and dried at room temperature.…”

Section: Methods and Instrumentsmentioning

confidence: 96%

Novel ESIPT fluorescent benzazolyl-4-quinolones: Synthesis, spectroscopic characterization and photophysical properties

et al. 2010

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New fluorescent monomers and polymers displaying an intramolecular proton-transfer mechanism in the electronically excited state (ESIPT), 1. Synthesis of benzazolylvinylene derivatives and its copolymerization with methyl methacrylate (MMA)

Cited by 40 publications

References 8 publications

Synthesis, characterization and photophysical properties of ESIPT reactive triazine derivatives

Synthesis, characterization and photophysical properties of ESIPT reactive triazine derivatives

In vitro antifungal activity of 2‐(2′‐hydroxy‐5′‐aminophenyl)benzoxazole in Candida spp. strains

Novel ESIPT fluorescent benzazolyl-4-quinolones: Synthesis, spectroscopic characterization and photophysical properties

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