Solvent effects and photophysical studies of a new class of acridine(1,8)dione dyes

Karunakaran, V.; Ramamurthy, P.; Josephrajan, T.; Ramakrishnan, V. T.

doi:10.1016/s1386-1425(01)00599-6

Cited by 27 publications

(13 citation statements)

References 32 publications

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“…However, applications have been limited to instrument sensitivity and applicable only for simple molecules. The solvatochromic method offers the simplest method to determine the dipole moments and is based on the shift of absorption and fluorescence maxima in different solvents yield fairly satisfactory results [19]. The solvent dependence of absorption and fluorescence maxima is used to estimate the excited state dipole moment.…”

Section: Introductionmentioning

confidence: 99%

Ground and excited state dipole moments of coumarin 337 laser dye

Raikar

Tangod

Mannopantar

et al. 2010

Optics Communications

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Section: Introductionmentioning

confidence: 99%

Ground and excited state dipole moments of coumarin 337 laser dye

Raikar

Tangod

Mannopantar

et al. 2010

Optics Communications

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“…Acridine (1,8)diones are a well-known class of compounds and have found many interesting applications. They exhibit excellent photo-physical properties, 16 making them ideal candidates to be used as laser dyes. 17 Acridine (1,8)diones are used as photosensitizers 18 and as photoinitiators in polymerisation reactions.…”

Section: Introductionmentioning

confidence: 99%

Acridinedione as selective flouride ion chemosensor: a detailed spectroscopic and quantum mechanical investigation

et al. 2018

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The use of small molecules as chemosensors for ion detection is rapidly gaining popularity by virtue of the advantages it offers over traditional ion sensing methods. Herein we have synthesized a series of acridine(1,8)diones (7a-7l) and explored them for their potential to act as chemosensors for the detection of various anions such as fluoride (F À ), acetate (OAc À ), bromide (Br À ), iodide (I À ), bisulfate (HSO 4 À ), chlorate (ClO 3 À ), perchlorate (ClO 4 À ), cyanide (CN À ), and thiocyanate (SCN À ). Acridinediones were found to be highly selective chemosensors for fluoride ions only. To investigate in detail the mechanism of selective fluoride ion sensing, detailed spectroscopic studies were carried out using UVvisible, fluorescence and 1 H NMR spectroscopy. Fluoride mediated (NH) proton abstraction of acridinedione was found to be responsible for the observed selective fluoride ion sensing. Quantum mechanical computational studies, using time dependent density functional theory (TDDFT) were also carried out, whereupon comparison of acridinedione interaction with fluoride and acetate ions explained the acridinedione selectivity for the detection of fluoride anions. Our results provide ample evidence and rationale for further modulation and exploration of acridinediones as non-invasive chemosensors for fluoride ion detection in a variety of sample types.An oven dried round bottom ask was charged with N-alkyl (Me/ Et) morpholine (1 g, 10 mmol, 1 equiv.) and toluene (5 mL). Subsequently, corresponding alkyl (C 5 , C 7 ) bromide (1.5 equiv.) Fig. 8 Overlay UV-vis absorption spectrum of 7i and fluoride complex 7i-F À , calculated at TD-B3LYP/6-31G(d,p).This journal is

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“…The fluorescence emission of acridine derivatives have, in the main, been reported to decay monexponentially with the lifetime showing a dependency on solvent 20,30 and substituent groups. 31,32 In strongly hydrogen bonding solvents, such as water, lifetimes over 10 ns have been reported. 20,2130,[33][34] The photocleavage is expected to proceed via the formation of an ion pair, which can undergo either a recombination to the initial ester or complete the cleavage with formation of photoproducts (Scheme 1).…”

Section: Additionally To Monitoring the Photolysis Process By Hplc/uvmentioning

confidence: 99%

“…The decay kinetics were clearly non exponential, unlike other studies on acridine derivatives. [30][31][32] The sum of three exponentials was required to provide a good fit to the data and is indicative of the more complex decay kinetics, even within our model for the photocleaved product. The outcome of the analysis is presented in Table 3.…”

Section: Additionally To Monitoring the Photolysis Process By Hplc/uvmentioning

confidence: 99%

Acridinyl methyl esters as photoactive precursors in the release of neurotransmitteramino acids

Piloto

Hungerford

Costa

et al. 2013

Photochem Photobiol Sci

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An investigation of the use of an azaheterocycle, acridine, as an alternative photochemically removable protecting group for the carboxylic function of neurotransmitter amino acids was carried out. 9-Bromomethylacridine was used in the reaction with glycine, alanine, glutamic acid, β-alanine and γ-aminobutyric acid, to obtain model ester derivatives, which were irradiated at different wavelengths in a photochemical reactor. The process was followed by HPLC/UV, resulting in the release of the active molecule in short irradiation times. The results obtained using 419 nm irradiation show promise (35-98 min) for practical purposes. The compounds were further characterised via time-resolved fluorescence to elucidate their photophysical properties and determine the decay kinetics.

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Solvent effects and photophysical studies of a new class of acridine(1,8)dione dyes

Cited by 27 publications

References 32 publications

Ground and excited state dipole moments of coumarin 337 laser dye

Ground and excited state dipole moments of coumarin 337 laser dye

Acridinedione as selective flouride ion chemosensor: a detailed spectroscopic and quantum mechanical investigation

Acridinyl methyl esters as photoactive precursors in the release of neurotransmitteramino acids

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