Synthesis, optical characterization and crystal and molecular X-ray structure of a phenylazojulolidine derivative

Barbero, Nadia; Barolo, Claudia; Marabello, Domenica; Buscaino, Roberto; Gervasio, Giuliana; Viscardi, G.

doi:10.1016/j.dyepig.2011.09.001

Cited by 6 publications

(2 citation statements)

References 40 publications

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“…Heteropolycycles based on julolidine are extremely valuable and are applied in industry and also in biological systems, such as photoconductive materials,25 nonlinear optical materials,26,27 highly fluorescent molecular rotors,28,29 chemiluminescent dyes,30,31 chromogenic substrates in analytical redox reactions,32 potential antidepressants and tranquilizers 33. Considering the importance of the julolidine structural motif, the synthesis of new structurally diverse julolidine derivatives that can benefit from its properties represents a challenge27,34,35 and, recently, the first synthesis of a julolidine‐fused heteroaromatic with coumarin has been reported for application as a fluorescent label 36…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Release of Neurotransmitter Amino Acids from Coumarin‐Fused Julolidine Ester Cages

Piloto¹,

Hungerford²,

Costa³

et al. 2013

Eur J Org Chem

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The photoinduced release of several neurotransmitter amino acids (glycine, alanine, glutamic acid, β‐alanine and γ‐aminobutyric acid) was accomplished from ester cages based on a new photoremovable protecting group consisting of a coumarin built on the julolidine nucleus, namely a (11‐oxo‐2,3,5,6,7,11‐hexahydro‐1H‐pyrano[2,3‐f]pyrido[3,2,1‐ij]quinolin‐9‐yl)methyl group. Photolysis and steady‐state sensitization studies revealed that release of the active molecule occurred in short irradiation times at long wavelengths, with a very promising performance at 419 nm. Given the interest in the development of novel protecting groups that are cleavable with UV A or even visible radiation, it was found that a structural modification in the coumarin ring by assembly of a fused julolidine leads to a promising photolabile protecting group for organic synthesis and also for bioapplications.

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Section: Introductionmentioning

confidence: 99%

Photoinduced Release of Neurotransmitter Amino Acids from Coumarin‐Fused Julolidine Ester Cages

Piloto¹,

Hungerford²,

Costa³

et al. 2013

Eur J Org Chem

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“…Other reactions at position C‐9 of the julolidine ring have been reported, including the synthesis of azocompounds performed Barbero et al (2012) and Salvador et al (2009) . In the first, the diazonium salt generated in situ reacted with julolidine hydrobromide in acidic medim (pH ≈ 4) (Scheme ) .…”

Section: Reactions From Julolidinesmentioning

confidence: 99%

Synthesis and Derivatization of Julolidine: A Powerful Heterocyclic Structure

Varejão

Fernandes

2019

Eur J Org Chem

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Julolidines constitute a class of N‐heterocycle compounds which have in common the 2,3,6,7‐tetrahydro‐1H,5H‐benzo[1,2]quinolizine ring. Due mainly to its fluorescence properties, such structures have shown potential application in a range of scientific and technological areas and have attracted attention of a great variety of research groups. For example, julolidines have been used for detection of ions and volatile compounds in environmental and biological samples, to the construction of dye‐sensitized solar cells, photoconductive materials and as fluorescent sensors for bioimaging. This review summarizes the strategies reported to the synthesis of the julolidine ring and the principal modifications for obtaining more complex julolidine derivatives with improved fluorescence properties of these compounds. In this context, aldol condensation, olefination, imine synthesis, and cross‐coupling reactions have been extensively explored and discussed. Examples of applications, which illustrate the great potential of such structures, will also be briefly presented.

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Three Heterocyclic Rings Fused (6-6-6)

Mojzych

2022

Comprehensive Heterocyclic Chemistry IV

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Synthesis, optical characterization and crystal and molecular X-ray structure of a phenylazojulolidine derivative

Cited by 6 publications

References 40 publications

Photoinduced Release of Neurotransmitter Amino Acids from Coumarin‐Fused Julolidine Ester Cages

Photoinduced Release of Neurotransmitter Amino Acids from Coumarin‐Fused Julolidine Ester Cages

Synthesis and Derivatization of Julolidine: A Powerful Heterocyclic Structure

Three Heterocyclic Rings Fused (6-6-6)

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