1-Bromo-3,3,3-trifluoro-1-nitropropene: Synthesis and reaction with phenyl azide

<p>Functional integration of proteins with carbon-based nanomaterials such as nanotubes holds great promise in emerging electronic and optoelectronic applications. Control over protein attachment poses a major challenge for consistent and useful device fabrication, especially when utilizing single/few molecule properties. Here, we exploit genetically encoded phenyl azide photochemistry to define the direct covalent attachment of three different proteins, including the fluorescent protein GFP, to carbon nanotube side walls. Single molecule fluorescence revealed that on attachment to SWCNTs GFP’s fluorescence changed in terms of intensity and improved resistance to photobleaching; essentially GFP is fluorescent for much longer on attachment. The site of attachment proved important in terms of electronic impact on GFP function, with the attachment site furthest from the functional center having the larger effect on fluorescence. Our approach provides a versatile and general method for generating intimate protein-CNT hybrid bioconjugates. It can be potentially applied easily to any protein of choice; attachment position and thus interface characteristics with the CNT can easily be changed by simply placing the phenyl azide chemistry at different residues by gene mutagenesis. Thus, our approach will allow consistent construction and modulate functional coupling through changing the protein attachment position.</p>

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Semiempirical description of the C6H5N reactive intermediate in phenyl azide photolysis

Theoretica Chimica Acta ◽

10.1007/bf00547253 ◽

1976 ◽

Vol 43 (2) ◽

pp. 137-144 ◽

Cited By ~ 6

Author(s):

Donald D. Shillady ◽

Carl Trindle

Keyword(s):

Reactive Intermediate ◽

Phenyl Azide

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Functional modulation and directed assembly of an enzyme through designed non-natural post-translation modification

Chemical Science ◽

10.1039/c4sc03900a ◽

2015 ◽

Vol 6 (7) ◽

pp. 3712-3717 ◽

Cited By ~ 11

Author(s):

Andrew M. Hartley ◽

Athraa J. Zaki ◽

Adam R. McGarrity ◽

Cecile Robert-Ansart ◽

Andriy V. Moskalenko ◽

...

Keyword(s):

Enzyme Activity ◽

Click Chemistry ◽

Directed Assembly ◽

Phenyl Azide ◽

Functional Modulation

Designed phenyl azide incorporation combined with bioorthogonal Click chemistry to regulate enzyme activity, or promote its stable assembly on graphene.

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ChemInform Abstract: Chemical Activation in Azide and Nitrene Chemistry: Methyl Azide, Phenyl Azide, Naphthyl Azides, Pyridyl Azides, Benzotriazoles, and Triazolopyridines

ChemInform ◽

10.1002/chin.201346230 ◽

2013 ◽

Vol 44 (46) ◽

pp. no-no

Author(s):

Curt Wentrup

Keyword(s):

Chemical Activation ◽

Phenyl Azide ◽

Nitrene Chemistry

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ChemInform Abstract: Intramolecular Ring Formation of Phenyl Azide and Furan Moieties.

Chemischer Informationsdienst ◽

10.1002/chin.198228072 ◽

1982 ◽

Vol 13 (28) ◽

Author(s):

K. YAKUSHIJIN ◽

T. TSURUTA ◽

H. FURUKAWA

Keyword(s):

Ring Formation ◽

Phenyl Azide ◽

Intramolecular Ring

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Pyrolysis of aryl azides. II. Naphthyl azides

Australian Journal of Chemistry ◽

10.1071/ch9720599 ◽

1972 ◽

Vol 25 (3) ◽

pp. 599 ◽

Cited By ~ 6

Author(s):

G Boshev ◽

LK Dyall ◽

PR Sadler

Keyword(s):

Nitro Group ◽

Steric Effect ◽

Kinetic Studies ◽

Oxidative Cyclization ◽

Nitrobenzene Solution ◽

Aryl Azides ◽

Phenyl Azide ◽

Group Participation ◽

Neighbouring Group Participation ◽

Group Effects

Kinetic studies of the pyrolyses of 1- and 2-naphthyl azides reveal neighbouring group participation by nitro and phenylazo substituents. The acceleration observed in 1-nitro-2-naphthyl azide, 1-phenylazo-2-naphthyl azide, and 2-nitro-1-naphthyl azide is 1730-, 211-, and 23.6-fold, respectively, in nitrobenzene solution at 120�. These effects are all smaller than that of the 2-nitro group in phenyl azide (3370-fold), which is ascribed to the steric effect of the peri hydrogen at C8 in naphthyl azides. The sizes of these neighbouring group effects correlate with the success of oxidative cyclization of ortho-substituted naphthylamines with (diacetoxyiodo)benzene.

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