Trifluoroacetylazobenzene for optical and electrochemical detection of amines

Abstract

In this work, we demonstrate the solution processing of optical and electrochemical dye sensors based on 4-(dioctylamino)-4 0 -(trifluoroacetyl)azobenzene and its application in sensing different amine compounds.Distinct optical response of the sensors exposed to ammonia, tetramethylammonium hydroxide, ethylamine, cadaverine and putrescine (typical compounds upon the decomposition of proteins) is observed. Incorporation of inkjet deposited thin films of the dye as sensors in food packages of ground meat and salmon is found as a feasible route to detect the appearance of biogenic amines produced by the degrading food products. Furthermore, we demonstrate an electrochemical amine sensor based on (trifluoroacetyl)azobenzene dye added in carbon nanotube-Nafion® composites. The electrochemical sensor exploits the reaction between the dye and amines to detect amines in electrolytes, while the carbon nanotubes provide large surface for adsorption and also provide a percolating electrical network for allowing efficient charge transfer at the electrode electrolyte interface. Scheme 1 Bonding reaction of 4-(dioctylamino)-4 0 -(trifluoroacetyl)azobenzene and amine. 4688 | J. Mater. Chem. A, 2015, 3, 4687-4694 This journal is

Chromogenic Signaling of Amine and Diamine with Hyperbranched Polymer Bearing (Trifluoroacetyl)azobenzene Surface Units

“…It is also suggests that probably two intramolecular hydrogen bonds arising from the simultaneous involvement of two hydroxyl groups may contribute to the stability of the proposed additional structure 9 . This structural mode is in line with the earlier proposal for the reaction of diamine with two trifluoroacetyl groups of 3‐3′‐di(trifluoroacetyl)‐1,1′‐bi‐2‐naphthol. Moderate to weak responses to primary monoamines such as ethanolamine, n ‐propylamine and benzylamine further demonstrate the role of aditional amino group in stabilizing the carbinolamine intermediate.…”

“…The colorimetric change of (trifluoroacetyl) azobenzene forming carbinolamine upon addition of aliphatic primary amine has been well described in the literature . Thus the marked selectivity of 4 for aliphatic primary diamine like ethylenediamine may be attributed to the formation of intramolecularly hydrogen bonded ring structure 7 involving other amino group with the hydroxyl group of carbinolamine moiety (Scheme ).…”

“…Colorimetric sensors are especially promissing because of their capability for easy naked eye detection requiring inexpensive instruments. (Trifluoroacetyl)azobenzene dyes have attracted considerable interest from chemists, principally because of their ability to change color upon exposure to amines . While a number of simple synthetic probes bearing such chromogenic reporter groups are available for sensing of amines, synthesis of amine indicating hyperbranched macromolecules is really a great challenge.…”

Endogenous and food-derived polyamines: determination by electrochemical sensing

“…The nanomaterial has stimulated the interest for the fabrication of electrochemical biosensors due to its unique combination of excellent mechanical, chemical and electrical properties (Yang et al 2013). Lin et al (2015) developed an electrochemical sensor based on (trifluoroacetyl)azobenzene, which reacts with amine compounds, coupled to carbon nanotubes on a glassy carbon electrode. The chemiresistor approach, based on cobalt porphyrins-single wall carbon nanotubes (SWCNTs)-gold electrodes already presented in paragraph 3.1, was brilliantly employed for the detection of volatile PUT and CAD at subppm concentrations in chicken and pork meat samples (Liu et al 2015).…”

Solid Polymer Substrates and Coated Fibers Containing 2,4,6‐Trinitrobenzene Motifs as Smart Labels for the Visual Detection of Biogenic Amine Vapors

“…This is especially true with sensors with chromogenicr esponse, that is, in which the presence of at arget chemical induces ac olor change, so that the human eye acts as detector. [1] Furthermore, if the sensori s ap olymer,t he material can be processed in different and manageable shapes as smartl abels, for instance, as films or textiles. [2] Among target molecules,b iogenic amines (BAs) are of special interest, specifically if they can be detected in the vapor phase, because their increasei np ackaged food, especially fish and meat, is related with the food freshness.…”