Styrylbenzodiazinones 1. Synthèse, structure et propriétés photophysiques

1993 ◽  
Vol 71 (12) ◽  
pp. 2007-2015 ◽  
Author(s):  
Louis Cazaux ◽  
Mourad Faher ◽  
Claude Picard ◽  
Pierre Tisnès
Keyword(s):  
Structural Study ◽  
Molecular Modelling ◽  
Fluorescent Dyes ◽  
Photophysical Properties ◽  
Rotational Isomerism ◽  
Derivatives Of ◽  
C Nmr

Several 3-styryl derivatives of 1,4-benzodiazine-2-one and of 1-methyl-1,4-benzodiazine-2-one were prepared. A structural study of these compounds by 1H and 13C NMR and by molecular modelling was carried out. The rotational isomerism around the bond connecting the imine and vinyl groups in these E styrylbenzodiazinones is discussed. The s-cis rotamer is shown to be the predominant isomer. The photophysical properties of these fluorescent dyes are reported.

Styrylbenzodiazinones 2. Chromo- et fluoroionophores dérivés du monoaza-15-couronne-5. Synthèse et structure

1993 ◽  
Vol 71 (8) ◽  
pp. 1236-1246 ◽  
Author(s):  
Louis Cazaux ◽  
Mourad Faher ◽  
Claude Picard ◽  
Pierre Tisnès
Keyword(s):  
Structural Study ◽  
Molecular Modelling ◽  
Acetonitrile Solution ◽  
Alkylation Reaction ◽  
Uv Spectrophotometry ◽  
Metallic Ions ◽  
Reversible Process ◽  
Derivatives Of ◽  
C Nmr

In connection with our work on styryl derivatives of benzodiazinones, we have prepared the 7-N,N-dimethylamino-3-methyl-1,4-benzodiazin-2-one 4a and two chromo- and fluoroionophores derived from the monoaza-15-crown-5 and styrylbenzodiazinones. A structural study of these compounds by 1H and 13C NMR, UV spectrophotometry, and molecular modelling was carried out. Unlike styrylbenzoxazinones, styrylbenzodiazinone derivatives showed a Z/E isomerization in acetonitrile solution. The isomerization was photoinduced, was catalysed by metallic ions, and was a reversible process. As well, an efficient alkylation reaction of the lactam function of benzodiazinones is described.

scholarly journals Substituent and Solvent Polarity on the Spectroscopic Properties in Azo Derivatives of 2-Hydroxynaphthalene and Their Difluoroboranes Complexes

Materials ◽  
2021 ◽  
Vol 14 (12) ◽  
pp. 3387
Author(s):  
Agnieszka Skotnicka ◽  
Przemysław Czeleń
Keyword(s):  
Spectral Properties ◽  
Nmr Spectra ◽  
Fluorescent Dyes ◽  
Photophysical Properties ◽  
Solvent Polarity ◽  
Spectroscopic Properties ◽  
Azo Group ◽  
Group Rotation ◽  
Derivatives Of ◽  
Substituted 1

Novel fluorescent dyes such as difluoroborane complexes of 1-phenylazonaphthalen-2-ol derivatives were successfully synthesized and characterized with a focus on the influence of a substituent and a solvent on the basic photophysical properties. 1H, 11B, 13C, 15N, and 19F nuclear magnetic resonance (NMR) spectra of substituted 1-phenylazonaphthalen-2-ol difluoroboranes and their parent azo dyes were recorded and discussed. The absorption and emission properties of synthesized compounds were investigated in solvents of varying polarity. They were found to be fluorescent despite the presence of the azo group. The azo group rotation was blocked by complexing with -BF2 to get a red shift in absorption. Solvent-dependent spectral properties of compounds were investigated using Lipper-Mataga and Bakhshiev plot. The calculated DFT energies and Frontier Molecular Orbitals calculations of the studied compounds were proved to be consistent with the experimental observations.

Thermal cyclocondensations of 3-N(4- and 5-benzimidazolyl and benztriazolyl)amino derivatives of 2-propenoic acid

1987 ◽  
Vol 52 (12) ◽  
pp. 2918-2925 ◽  
Author(s):  
Viktor Milata ◽  
Dušan Ilavský
Keyword(s):  
Uv Spectra ◽  
Propenoic Acid ◽  
Amino Derivatives ◽  
Derivatives Of ◽  
C Nmr ◽  
Ir And Uv Spectra

The cyclization of 3-N(4- and 5-benzimidazolyl and benztriazolyl)amino-2-cyano- and 2-ethoxycarbonyl-2-propenoate esters Ia, b-IVa, b under the conditions of the Gould-Jacobs reaction leads to angularly ring-fused substituted imidazo or triazolo[4,5-f] (V, VI) and [4,5-h] (VII, VIII) quinolines, respectively. The esters Vb-VIIIb have been transformed into the corresponding chloroderivatives Vc-VIIIc. 3-N(5-Benzimidazolyl and 5-benztriazolyl)amino-2-cyano-2-propenenitriles are cyclized in the presence of aluminium(III) chloride to give the aminoquinolines Vd, VId. The structure of the products has been characterized by their 1H, 13C NMR, IR, and UV spectra.

scholarly journals Core-Substituted Naphthalene-diimides (cNDI) and Related Derivatives: Versatile Scaffold for Supramolecular Assembly and Functional Materials

2021 ◽  
Author(s):  
Anurag Mukherjee ◽  
Suhrit Ghosh
Keyword(s):  
Photophysical Properties ◽  
Supramolecular Assembly ◽  
Functional Materials ◽  
Building Blocks ◽  
Short Review ◽  
Molecular Engineering ◽  
Organic Optoelectronics ◽  
Naphthalene Diimide ◽  
Naphthalene Diimides ◽  
Derivatives Of

Naphthalene-diimide (NDI) derived building blocks have been explored extensively for supramolecular assembly as they exhibit attractive photophysical properties, suitable for applications in organic optoelectronics. Core-substituted derivatives of the NDI chromophore (cNDI) differ significantly from the parent NDI dye in terms of optical and redox properties. Adequate molecular engineering opportunities and substitution-dependent tunable optoelectronic properties make cNDI derivatives highly promising candidates for supramolecular assembly and functional material. This short review discusses recent development in the area of functional supramolecular assemblies based on cNDIs and related molecules.

Preparation of 2,3-Dideoxy-2,3-epimino and 3,4-Dideoxy-3,4-epimino Derivatives of 1,6-Anhydro-β-D-hexopyranoses by Mitsunobu Reaction

1998 ◽  
Vol 63 (6) ◽  
pp. 813-825 ◽  
Author(s):  
Jiří Kroutil ◽  
Tomáš Trnka ◽  
Miloš Buděšínský ◽  
Miloslav Černý
Keyword(s):  
Nmr Spectra ◽  
Mitsunobu Reaction ◽  
Derivatives Of ◽  
C Nmr

A series of new 2-, 3- and 4-benzylamino-2-, 3- and 4-deoxy derivatives of 1,6-anhydro-β-D-hexopyranoses were prepared from 1,6:2,3- and 1,6:3,4-dianhydro-β-D-hexopyranoses by treatment with benzylamine and converted into 2,3-(N-benzylepimino)-2,3-dideoxy- and 3,4-(N-benzylepimino)-3,4-dideoxy-β-D-hexopyranoses of the D-allo, D-galacto and D-talo configuration by Mitsunobu reaction. The structures of benzylamino and benzylimino derivatives were confirmed by 1H and 13C NMR spectra.

Triazene derivatives of (1,x-)diazacycloalkanes. Part VI. 3-({5,5-Dimethyl-3-[2-aryl-1-diazenyl]-1-imidazolidinyl}methyl)-4,4-dimethyl-1-[2-aryl-1-diazenyl]imidazolidines — Synthesis, characterization, and X-ray crystal structure

2006 ◽  
Vol 84 (10) ◽  
pp. 1294-1300 ◽  
Author(s):  
Keith Vaughan ◽  
Shasta Lee Moser ◽  
Reid Tingley ◽  
M Brad Peori ◽  
Valerio Bertolasi
Keyword(s):  
Crystal Structure ◽  
Significant Degree ◽  
Ion Trapping ◽  
Published Data ◽  
X Ray ◽  
X Ray Crystallography ◽  
Diazonium Ion ◽  
Derivatives Of ◽  
C Nmr

Reaction of a series of diazonium salts with a mixture of formaldehyde and 1,2-diamino-2-methylpropane affords the 3-({5,5-dimethyl-3-[2-aryl-1-diazenyl]-1-imidazolidinyl}methyl)-4,4-dimethyl-1-[2-aryl-1-diazenyl]imidazolidines (1a–1f) in excellent yield. The products have been characterized by IR and NMR spectroscopic analysis, elemental analysis, and X-ray crystallography. The X-ray crystal structure of the p-methoxycarbonyl derivative (1c) establishes without question the connectivity of these novel molecules, which can be described as linear bicyclic oligomers with two imidazolidinyl groups linked together by a one-carbon spacer. This is indeed a rare molecular building block. The molecular structure is corroborated by 1H and 13C NMR data, which correlates with the previously published data of compounds of types 5 and 6 derived from 1,3-propanediamine. The triazene moieties in the crystal of 1c display significant π conjugation, which gives the N—N bond a significant degree of double-bond character. This in turn causes restricted rotation around the N—N bond, which leads to considerable broadening of signals in both the 1H and 13C NMR spectra. The molecular ion of the p-cyanophenyl derivative (1b) was observed using electrospray mass spectrometry (ES + Na). The mechanism of formation of molecules of type 1 is proposed to involve diazonium ion trapping of the previously unreported bisimidazolidinyl methane (13).Key words: triazene, bistriazene, imidazolidine, synthesis, X-ray crystallography, NMR spectroscopy.

scholarly journals Perylene-like Dyes in Liquid Crystalline Media

1996 ◽  
Vol 51 (7) ◽  
pp. 843-850 ◽  
Author(s):  
Ewa Mykowska ◽  
Danuta Bauman
Keyword(s):  
Phase Transition ◽  
Transition Temperature ◽  
Order Parameter ◽  
Liquid Crystalline ◽  
Fluorescent Dyes ◽  
Liquid Crystal Display ◽  
Isotropic Phase ◽  
Display Devices ◽  
Electrooptical Properties ◽  
Derivatives Of

Abstract The spectral and electrooptical properties of some dichroic fluorescent dyes (derivatives of 3.4,9,10-perylenetetracorboxylic acid and of 3,4,9-perylenetricarboxylic acid) in isotropic solvents and nematic liquid crystals have been studied. The order parameter of the dyes in the anisotropic matrices has been determined by means of optical spectroscopy methods. Moreover, the influence of the dye addition on the nematic-isotropic phase transition temperature of the pure host has been investigated. It was found that some of the dyes studied can be utilized in guest-host liquid crystal display devices.

Beziehungen zwischen Rotationsisomerie, Wasserstoffbrücken-Bindung und Substituenteneffekten der organischen Chemie / Relations between Rotational Isomerism, Hydrogen Bonding, and Substituent Effects in Organic Chemistry

1972 ◽  
Vol 27 (6) ◽  
pp. 663-674 ◽  
Author(s):  
Gotthard H. Krause ◽  
Herbert Hoyer
Keyword(s):  
Hydrogen Bonding ◽  
Substituent Effects ◽  
Intramolecular Hydrogen Bonding ◽  
Rotational Isomerism ◽  
Proton Acceptor ◽  
Single Bond ◽  
Free Enthalpy ◽  
Acceptor Group ◽  
Intramolecular Hydrogen ◽  
Derivatives Of

The change of free enthalpy involved in intramolecular hydrogen bonding is smaller if the proton acceptor group can rotate round a single bond, as compared to proton acceptor groups which are fixed in a position optimal for hydrogen bonding. Also, the free enthalpy change is altered when the rotation of the proton acceptor is sterically restricted. This is demonstrated by comparing the absorptions of carbonyl stretching vibrations in the infrared spectra of certain compounds showing rotational isomerism. In the present study derivatives of 5-hydroxy-2,2-dimethyl-6-carbomethoxychromanone- (4), 3-nitrosalicylaldehyde and 3-nitro-2-hydroxy-acetophenones substituted in the position 5 and 6 are examined.

scholarly journals Accurate Determination of Human CPR Conformational Equilibrium by smFRET using Dual Orthogonal Non-Canonical Amino Acid Labeling

2018 ◽  
Author(s):  
Robert B. Quast ◽  
Fataneh Fatemi ◽  
Michel Kranendonk ◽  
Emmanuel Margeat ◽  
Gilles Truan
Keyword(s):  
Single Molecule ◽  
Conformational Equilibrium ◽  
Fluorescent Dyes ◽  
Photophysical Properties ◽  
Accurate Determination ◽  
Conformational Dynamics ◽  
Resonance Energy Transfer ◽  
Resonance Energy ◽  
General Strategy

ABSTRACTConjugation of fluorescent dyes to proteins - a prerequisite for the study of conformational dynamics by single molecule Förster resonance energy transfer (smFRET) - can lead to substantial changes of the dye’s photophysical properties, ultimately biasing the quantitative determination of inter-dye distances. In particular the popular cyanine dyes and their derivatives, which are by far the most used dyes in smFRET experiments, exhibit such behavior. To overcome this, a general strategy to site-specifically equip proteins with FRET pairs by chemo-selective reactions using two distinct non-canonical amino acids simultaneously incorporated through genetic code expansion in Escherichia coli was developed. Applied to human NADPH- cytochrome P450 reductase (CPR), the importance of homogenously labeled samples for accurate determination of FRET efficiencies was demonstrated. Furthermore, the effect of NADP+ on the ionic strength dependent modulation of the conformational equilibrium of CPR was unveiled. Given its generality and accuracy, the presented methodology establishes a new benchmark to decipher complex molecular dynamics on single molecules.

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