Synthesis of new fluorescent molecules having an aggregation-induced emission property derived from 4-fluoroisoxazoles

Fluorescent molecules based on a fluorinated isoxazole scaffold were provided for the synthetic methods and their photochemical properties. Simple 3,5-diarylisoxazoles led to increasing the fluorescent intensity and exhibited a redshift in the emission intensity by introducing a fluorine atom. α-Fluorinated boron ketoiminates (F-BKIs) derived from a ring opening reaction of 4-fluoroisoxazoles were also synthesized and exhibited a highly fluorescent luminescence as a new aggregation-induced emission (AIE) fluorophore.

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Synthesis of new fluorescent molecules having an aggregation-induced emission property derived from 4-fluoroisoxazoles

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.16.117 ◽

2020 ◽

Vol 16 ◽

pp. 1411-1417 ◽

Cited By ~ 2

Author(s):

Kazuyuki Sato ◽

Akira Kawasaki ◽

Yukiko Karuo ◽

Atsushi Tarui ◽

Kentaro Kawai ◽

...

Keyword(s):

Fluorescence Intensity ◽

Emission Intensity ◽

Ring Opening ◽

Emission Property ◽

Aggregation Induced Emission ◽

Ring Opening Reaction ◽

Photochemical Properties ◽

Fluorescent Molecules

Fluorescent molecules based on a fluorinated isoxazole scaffold were synthesized and investigated for their photochemical properties. The introduction of a fluorine substituent into 3,5-diarylisoxazoles led to an increase of fluorescence intensity and exhibited a redshift in the emission intensity. α-Fluorinated boron ketoiminates (F-BKIs) were also synthesized via a ring-opening reaction of 4-fluoroisoxazoles and exhibited highly fluorescent luminescence and aggregation-induced emission (AIE), showing promise as a new fluorophore.

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Fabrication of cross-linked fluorescent polymer nanoparticles and their cell imaging applications

Journal of Materials Chemistry C ◽

10.1039/c4tc02672a ◽

2015 ◽

Vol 3 (8) ◽

pp. 1854-1860 ◽

Cited By ~ 31

Author(s):

Ke Wang ◽

Xiaoyong Zhang ◽

Xiqi Zhang ◽

Bin Yang ◽

Zhen Li ◽

...

Keyword(s):

Free Radical ◽

Radical Polymerization ◽

Ring Opening ◽

Cell Imaging ◽

Free Radical Polymerization ◽

Polymer Nanoparticles ◽

Aggregation Induced Emission ◽

Ring Opening Reaction ◽

Fluorescent Polymer

Fabrication of aggregation induced emission dye based cross-linked fluorescent polymer nanoparticlesviafree radical polymerization and ring-opening reaction for bioimaging.

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Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.16.82 ◽

2020 ◽

Vol 16 ◽

pp. 904-916

Author(s):

Phil M Pithan ◽

Sören Steup ◽

Heiko Ihmels

Keyword(s):

Ring Opening ◽

Oxidation Reaction ◽

Mass Spectrometric ◽

Ring Closure ◽

Fluorimetric Detection ◽

Broad Absorption ◽

Broad Absorption Band ◽

Ring Opening Reaction ◽

Screening Assays ◽

Photochemical Properties

Two new spiroindolinonaphthoxazine derivatives with an electron-accepting styrylquinolizinium or styrylcoralyne unit, respectively, were synthesized, and the influence of such an arylvinyl substituent on the chemical and photochemical properties of the compounds was investigated. Specifically, these spirooxazines turned out to be resistant towards the photoinduced merocyanine formation, and the irradiation with light mainly led to photodegradation of the substrates. However, it was shown by colorimetric and fluorimetric screening assays as well as by detailed NMR spectroscopic and mass spectrometric studies that the addition of particular metal ions (Cu2+, Fe3+, and to a certain extent Hg2+) initially induced a ring-opening reaction that was irreversibly followed by a fast ring closure–deprotonation–oxidation sequence to give styryl-substituted naphthoxazole derivatives as the products quantitatively. For the quinolizinium-substituted spirooxazine derivative, the formation of the respective oxidation product caused the development of a broad absorption band between 425 nm and 500 nm and a new emission band at λfl = 628 nm, so that it may be employed as a selective chemosensor or chemodosimeter for the colorimetric and fluorimetric detection of Cu2+ and Fe3+.

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Selective preparation of tetrasubstituted fluoroalkenes by fluorine-directed oxetane ring-opening reactions

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.16.160 ◽

2020 ◽

Vol 16 ◽

pp. 1936-1946

Author(s):

Clément Q Fontenelle ◽

Thibault Thierry ◽

Romain Laporte ◽

Emmanuel Pfund ◽

Thierry Lequeux

Keyword(s):

Ring Opening ◽

Fluorine Atom ◽

Van Der Waals ◽

Ring Opening Reaction ◽

Ring Opening Reactions ◽

Bromide Ions ◽

Selective Ring Opening ◽

Oxetane Ring ◽

Van Der Waals Radii

The selective ring-opening reaction of fluoroalkylidene-oxetanes was directed by the presence of the fluorine atom, enabling a two-step access to tetrasubstituted fluoroalkenes with excellent geometry control. Despite its small van der Waals radii electronic, rather than steric influences of the fluorine atom governed the ring-opening reaction with bromide ions, even in the presence of bulky substituents.

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On the Conrotatory Ring Opening of 3-Carbomethoxycyclobutene Vis-À-Vis 3-Carbomethoxy-1,2-Benzocyclobutene and the Predominant Inward Opening of 3-Dimethylaminocarbonyl-1,2-Benzocyclobutene

10.26434/chemrxiv.7094003.v1 ◽

2018 ◽

Author(s):

Veejendra Yadav ◽

Dasari L V K Prasad ◽

Arpita Yadav ◽

Maddali L N Rao

Keyword(s):

Transition State ◽

Ring Opening ◽

Electron Process ◽

Ring Opening Reaction ◽

Stable Species ◽

Electron Event

The torquoselectivity of conrotatory ring opening of 3-carbomethoxycyclobutene is controlled by pC1C2→s*C3C4 and sC3C4→p*CO interactions in the transition state in a 4-electron process as opposed to only sC3C4→p*CO interaction in an apparently 8-electron event in 3-carbomethoxy-1,2-benzocyclobutene. The ring opening of 3-carbomethoxy-1,2-benzocyclobutene is sufficiently endothermic. We therefore argue that the reverse ring closing reaction is faster than the forward ring opening reaction and, thus, it establishes an equilibrium between the two and subsequently allows formation of the more stable species via outward ring opening reaction. Application of this argument to 3-dimethylaminocarbonyl-1,2-benzocyclobutene explains the predominantly observed inward opening.

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One-step preparation of cyclen-containing hydrophilic polymeric monolithic materials via epoxy-amine ring-opening reaction and their application in enrichment of N-glycopeptides

Talanta ◽

10.1016/j.talanta.2020.122049 ◽

2021 ◽

Vol 225 ◽

pp. 122049

Author(s):

Chen Ma ◽

Ruizhi Tang ◽

Yan Wang ◽

Shujuan Ma ◽

Shouwan Tang ◽

...

Keyword(s):

Ring Opening ◽

Epoxy Amine ◽

Ring Opening Reaction ◽

One Step

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Expanding Monomers as Anti-Shrinkage Additives

Polymers ◽

10.3390/polym13050806 ◽

2021 ◽

Vol 13 (5) ◽

pp. 806

Author(s):

Philipp Marx ◽

Frank Wiesbrock

Keyword(s):

Ring Opening ◽

Covalent Bond ◽

Volumetric Shrinkage ◽

Structure Property ◽

Atomic Packing ◽

Materials Properties ◽

Volumetric Expansion ◽

Structure Property Relationships ◽

Ring Opening Reaction ◽

Measuring Techniques

Commonly, volumetric shrinkage occurs during polymerizations due to the shortening of the equilibrium Van der Waals distance of two molecules to the length of a (significantly shorter) covalent bond. This volumetric shrinkage can have severe influence on the materials’ properties. One strategy to overcome this volumetric shrinkage is the use of expanding monomers that show volumetric expansion during polymerization reactions. Such monomers exhibit cyclic or even oligocyclic structural motifs with a correspondingly dense atomic packing. During the ring-opening reaction of such monomers, linear structures with atomic packing of lower density are formed, which results in volumetric expansion or at least reduced volumetric shrinkage. This review provides a concise overview of expanding monomers with a focus on the elucidation of structure-property relationships. Preceded by a brief introduction of measuring techniques for the quantification of volumetric changes, the most prominent classes of expanding monomers will be presented and discussed, namely cycloalkanes and cycloalkenes, oxacycles, benzoxazines, as well as thiocyclic compounds. Spiroorthoesters, spiroorthocarbonates, cyclic carbonates, and benzoxazines are particularly highlighted.

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Design and synthesis of 1,8-Naphthalimide Functionalized Benzothiadiazoles

New Journal of Chemistry ◽

10.1039/d1nj00919b ◽

2021 ◽

Author(s):

Rajneesh Misra ◽

Yogjivan Rout

Keyword(s):

Ring Opening ◽

Coupling Reaction ◽

Cross Coupling ◽

Design And Synthesis ◽

Cross Coupling Reaction ◽

Ring Opening Reaction

A series of multi acceptor based push-pull derivatives BTD2–BTD5 were designed and synthesized via Pd-catalyzed Sonogashira cross-coupling reaction followed by [2+2] cycloaddition–electrocyclic ring-opening reaction in which benzothiadiazole (BTD, A1), naphthalimide...

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(1R,4S,5S)-5-((3-Hydroxypropyl)amino)-4-((1-Methyl-1H-tetrazol-5-yl)thio)Cyclopent-2-en-1-ol

Molbank ◽

10.3390/m1199 ◽

2021 ◽

Vol 2021 (2) ◽

pp. M1199

Author(s):

Milene A. G. Fortunato ◽

Filipa Siopa ◽

Carlos A. M. Afonso

Keyword(s):

Spectral Data ◽

13C Nmr ◽

Ring Opening ◽

Environmentally Friendly ◽

Mass Spectral Data ◽

Mass Spectral ◽

Excellent Yield ◽

Ring Opening Reaction ◽

Nucleophilic Ring Opening

Using environmentally friendly conditions, the nucleophilic ring-opening reaction of 6-azabicyclo[3.1.0]hex-3-en-2-ol with 1-methyl-1H-tetrazole-5-thiol provided a novel thiol-incorporated aminocyclopentitol, (1R,4S,5S)-5-((3-hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol, in excellent yield (95%). The newly synthesized compound was analyzed and characterized via 1H, 13C-NMR, HSQC, and mass spectral data.

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