Crown ether-containing styryl dyes

Gromov, S. P.; Fomina, M. V.; Алфимов, М. В.

doi:10.1007/bf00699196

Cited by 7 publications

(15 citation statements)

References 5 publications

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“…To study the formation of complexes of trans- 17,18 with Mg 2+, titration of solutions of complexes with a solution of a competing ligand (BI5C5) was used, as in the case of anion-"capped" complexes (cis-17,18) 9 Mg 2~.…”

Section: Trans-isomersmentioning

confidence: 99%

Supramolecular organic photochemistry of crown-ether-containing styryl dyes

Gromov

Алфимов

1997

Russ Chem Bull

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Section: Trans-isomersmentioning

confidence: 99%

Supramolecular organic photochemistry of crown-ether-containing styryl dyes

Gromov

Алфимов

1997

Russ Chem Bull

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“…43 These compounds exhibit weak fluorescence in solution at room temperature (the fluorescence quantum yield ϕ f = 0.002-0.1). 49, 50 On the contrary, cis isomers of styryl dyes show no fluorescence at all.…”

Section: Fluorescence and Excimer Formationmentioning

confidence: 99%

Molecular meccano for light-sensitive and light-emitting nanosized systems based on unsaturated and macrocyclic compounds

Gromov

2008

Russ Chem Bull

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The review presents the results of the development of an universal approach to the molecular design of light sensitive and light emitting nanosized systems with desired properties based on unsaturated and macrocyclic compounds. Within the same class of compounds, various nanosized systems were constructed using a limited number of structural fragments. These nanosized systems are susceptible to all main types of photoprocesses, such as fluorescence, photodissociation, photo isomerization, photocycloaddition, photoelectrocyclization, excimer formation, charge transfer com plex formation, the formation of the twisted intramolecular charge transfer state (TICT state), and the electron transfer. The use of photostructural transformations for controlling the complexation and mechanical movements in molecular devices and machines is discussed. The prospects of application of the new strategy are exemplified by the design of the previously unknown types of molecular switches, materials for optical chemosensors, optical data recording and storage media, photo switchable molecular devices, and photocontrolled molecular machines.

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“…38,39 If the reaction between, for example, 1,2,4,6-tetramethyl-3-nitropyridinium iodide and acetone is carried out in an excess of an aqueous solution of methylamine, the yield of 1,2,4,6-tetramethylindole decreases to 3% because competing hydrolytic elimination of the amino group occurs in parallel, apparently, at the step where the open form exists. 38,39 If the reaction between, for example, 1,2,4,6-tetramethyl-3-nitropyridinium iodide and acetone is carried out in an excess of an aqueous solution of methylamine, the yield of 1,2,4,6-tetramethylindole decreases to 3% because competing hydrolytic elimination of the amino group occurs in parallel, apparently, at the step where the open form exists.…”

Section: Ring Transformations Of Nitropyridinium Salts Into Indolesmentioning

confidence: 99%

“…52,53 For instance, the reaction of 1,2,4,6-tetramethyl-3-nitropyridinium iodide (20) directly with acetone methylimine provides 1,2,4,6-tetramethylindole in the same yield as the reaction using an acetone solution of methylamine. 39 When investigating the reaction of nitropyridinium salts with ketimines in various solvents, authors 53 arrived at the conclusion that polar aprotic solvents such as DMF or pyridine substantially accelerate the indole formation, although the yield of indoles either does not change significantly in the presence of these solvents or even decreases. 44 Moreover, we found that a small amount of water is necessary for the reaction and increases the yields ofindoles.…”

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“…38 Evidently, these data do not rule out the possibility of direct reaction of nitropyridinium salts with ketones in water-containing media, as has been done previously. 39 However, the use of ketimines is relatively unpromising from the practical viewpoint because they are difficult to obtain; 54 and, in addition, the number of steps in the process 39 When investigating the reaction of nitropyridinium salts with ketimines in various solvents, authors 53 arrived at the conclusion that polar aprotic solvents such as DMF or pyridine substantially accelerate the indole formation, although the yield of indoles either does not change significantly in the presence of these solvents or even decreases.…”

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Ring Transformation of Pyridines and Benzo Derivatives under the Action of C-Nucleophiles

Gromov¹

2000

HETEROCYCLES

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The data on ring transformations of heterocyclic systems containing a pyridine ring on treatment with C-nucleophiles are generalized and described systematically over the period of up to 1999. CONTENTS I. Introduction II. Cyclopentadiene derivatives III. Ketones and enamines 1. Ring transformations of dinitropyridones 2. Ring transformations of nitropyridinium salts into indoles IV. β-Dicarbonyl compounds and carboxylic acids V. Nitroalkanes and sulfoxides VI. Conclusion I. INTRODUCTIONPyridine ring is relatively stable against cleavage, although it is less stable than benzene.The Zincke-König reaction, 1 i.e. cleavage of the quaternized pyridine ring on treatment with aromatic amines to give glutaconic dialdehyde dianils, was historically the first comprehensively studied example of this type of reaction. Subsequently, numerous ring transformations of the pyridine ring induced by nucleophiles have been discovered and studied. 2 They include, first of all, a number of new rearrangements some of which are general for the chemistry of heterocyclic compounds, such as the amidine rearrangement 3 and the enamine rearrangement of pyridine derivatives found in our study. 4 Nevertheless, no comprehensive and special review on ring transformations of the pyridine ring induced by C-nucleophiles have been published so far. Since the search for new types of ring transformations of heterocycles on treatment with Cnucleophiles remains a topical problem (see, for example, a review devoted to ring transformations of pyrimidines 5 ) and the interest of synthetic chemists in the development of original synthetic procedures based on these reactions persists, it appears pertinent to follow the development and the characteristic features of studies carried out along this line.Carbanions are species presenting considerable interest, first of all, due to the fact that they have diverse structures and functional groups and thus they are potentially capable of being incorporated according to various patterns into molecules formed in the ring transformations of the pyridine ring.Carbanions are mild nucleophiles; therefore, they mainly add to a pyridine ring at position 4 rather than 2. 6-9 The resulting 1,4-dihydropyridines cannot undergo electrocyclic cleavage of the pyridine ring because it is possibleonly for 1,2-dihydropyridine derivatives. Apparently, this fact hampers the conduction of ring transformations of pyridine derivatives induced by C-nucleophiles. This is partly responsible for the fact that only few types of reactions involving carbanions can be found in the literature and are considered below. However, the great synthetic potential of ring transformations of the pyridine ring involving C-nucleophiles makes further efforts along this line not merely justified but even highly promising. II. CYCLOPENTADIENE DERIVATIVESThe first example of ring transformation of pyridinium salts on treatment with С-nucleophiles was represented by the Ziegler-Hafner synthesis 10,11 of azulenes; one variant of this reaction makes use of pyridin...

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Crown ether-containing styryl dyes

Cited by 7 publications

References 5 publications

Supramolecular organic photochemistry of crown-ether-containing styryl dyes

Supramolecular organic photochemistry of crown-ether-containing styryl dyes

Molecular meccano for light-sensitive and light-emitting nanosized systems based on unsaturated and macrocyclic compounds

Ring Transformation of Pyridines and Benzo Derivatives under the Action of C-Nucleophiles

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