1
Polymer Engineering and Color Technology Department, Amirkabir University of Technology
2
Mahshahr Campus, Amirkabir University of Technology
Abstract
Nowadays, the identification of amines is important because of the presence of these toxic substances in industrial, environmental and marine food corruption. A possible method for the identification of amine systems is based on dyes. The purpose of the chemical sensors is to identify how to eliminate these toxic substances. There are different colorimetric methods for the identification of amine compounds, which are fluorescence chemical sensors, an appropriate method for identification. Fluorescence is widely used in optical sensors, cellular imaging to detect cancer types and security issues. The effect of the environment, including the effect of the solvent, the protonation, the polarity of the conjugate fluorescence organic compounds, and the addition of the donar-acceptor substitute to the derivatives of Distyrylbenzene and the polymers combined with conjugated organic compounds, change the optical properties. Distyrylbenzene derivatives have fluorescence properties. Adding different substitute to these derivatives will change the emission spectrum. Among these, the oligo(p- phenylenevinylene) (OPV) as donar group and propylenebisimide (PBIs) as acceptor group, which, if aggrigated, increases the fluorescence quenching. To create a suitable sensor without leaking dye into the surface of polymer, a covalent bond between the polymer and the dye material should be established, which is created by two-stage dispersion polymerization . By adding these polymers to one of the derivatives of Distyrylbenzenedialdehyde, a sensor can be identified types of amines that change the color of the amine solution by changing the pH and polarity, different amines have different emission spectra. Of course, the identification of amine in solid state is better than solution, with increasing pH and polarity, batocromic shifts are observed. In general, the emission wavelengths of symmetric fluorescence conjugate compounds are highly sensitive to different amines and, by investigating the optical behavior of these compounds, it is possible to identify the amines.
J. Yao, M. Yang, Y. Duan, "Biology and medicine of fluorescent nanomaterials and related systems: new insights into biosensing, bioimaging, genomics, diagnostics, and therapy", Chem. Rev, 114, 6130-6178, 2014.
D. Rendell, "Fluorescence and Phosphorescence (Analytical Chemistry by Open Learning)", TBS, 1987.
J. Kumpf, S. Thimon Schwaebel, U. H. F. Bunz, "Amine detection with distyrylbenzenedialdehyde-based knoevenagel adducts",J. Org. Chem.80, 5159–5166, 2015.
P. L. McGrier, K. M. Solntsev, S. Miao, L. M. Tolbert, O. R. Miranda, V. M. Rotello, U. H. F. Bunz, "Hydroxycruciforms: amine-Responsive fluorophores", Chem. Eur. J. 14, 4503 – 4510, 2008.
J. Kumpf, J. Freudenberg, S. Thimon Schwaebel, U. H. F. Bunz, "Amine sensing with distyrylbenzenes and their hexamethylene-Linked polymers: spraying Them On", Macromol. 47, 2569−2573, 2014.
C. Patze, K. Broedner, F. Rominger, O. Trapp, U. H. F. Bunz, "Aldehyde cruciforms: dosimeters for primary and secondary amines", Chem. Eur. J. 17, 13720 – 13725, 2011.
J. Chen, F.Y. Yi, H. Yu, .S. Jiao, G. Pang, Z. Ming Sunb, "Fast response and highly selective sensing of amine vapors using a luminescent coordination polymer",Chem. Commun. 50, 10506-10509, 2014.
C. LX, H. XW, H. XB, H. Xu, "Calixarene-coated piezoelectric quartz crystal sensor for the detection of organic amine in liquids", Analyst, 124, 1787-1790, 1999.
L. Mattsson, J. Xu, C. Preininger, B. T Sum Bui, K. Haupt, "Competitive fluorescent pseudo-immunoassay exploiting molecularly imprinted polymers for the detection of biogenic amines in fish matrix", Talanta ,181,190-196, 2018.
S. D, Valiyaveettil, "Perylene derivatives as a fluorescent probe for sensing of amines in solution", Dyes. Pigm. 134,306-314, 2016.
J. Freudenberg, J. Kumpf, V. Schäfer, E. Sauter, S. J. Wörner, K. Brödner, A. Dreuw, U. H. F. Bunz, "Water-soluble cruciforms and distyrylbenzenes: synthesis, characterization, and pH-dependent amine-sensing properties",J. Org. Chem.78, 4949–4959, 2013.
M. V. Kiryukhin, H. Hong Lau, S. Hong Goh, C. Teh, V. Korzh, A. Sadovoy, "A membrane film sensor with encapsulated fluorescent dyes towards express freshness monitoring of packaged food", Talanta, 182, 187-192, 2018.
Z. Ma, P. Chen, W. Cheng, K. Yan, L. Pan, Y. Shi, . G. Yu, "Highly Sensitive, Printable nanostructured conductive polymer wireless sensor for food spoilage detection", Nano. Lett.18, 4570–4575, 2018.
J. Janata, , A. Bezegh, "Chemical sensors", Analitical. Chem. 60, 62-74,1988.
H. Hisamoto, K.Suzuki, "Ion-selective optides: current developments and future prospects", Trends. Analyt. Chem. 18, 513–524,1999.
L. Swapnil Sonawane, S. K. Asha, "Fluorescent cross-linked polystyrene perylenebisimide/ Oligo(p‑Phenylenevinylene) microbeads with controlled Particle Size, tunable Colors, and high Solid state emission", ACS Appl. Mater. Interfaces. 5, 12205−12214, 2013.
J. N. Wilson, U. H. F. Bunz,"Switching of intramolecular charge Transfer in cruciforms: metal ion sensing",J. Am. Chem. Soc. 127, 4124-4125, 2005.
M. T. Sharbati, F.Panahi, A. Gharavi, "Near-infrared organic light-emitting diodes based on donor-pi-acceptor oligomers", IEEE Photonics Technol. Lett. 22, 1695-1697, 2010.
J. R. Albani, "Principles and applications of fluorescence spectroscopy", John Wiley & Sons, 2007.
A. J. Zucchero, J. Tolosa, L. M. Tolbert, U.H. F. Bunz, "Bis (4’-dibutylaminostyryl)benzene: spectroscopic behavior upon protonation or methylation", Chem. Eur. J. 15, 13075 – 13081, 2009.
J. Du , N. Xie , X. Wang , L. Sun , Y. Zhao, F. Wu, "Optical limiting effects of cyano substituted distyrylbenzene derivatives", Dyes. Pigm. 134, 368-374, 2016.
J. H. Burroughes, D. D. C. Brdley, A. R. Brown, R. N. Marks, K. Mackay, R. H. Friend, P. L.Burns, A. B. Holmes, "Light-emmitting diodes based on conjugated polymers", Nature. 374,539-541, 1990.
S. Kumari Nisha, S. K. Asha, "Random Copolyesters Containing perylene Bisimide: flexible films and fluorescent fibers", ACS Appl. Mater. Interfaces. 6, 12457−12466, 2014.
G. G. Flores-Rojas, Irina V. Lijanova, Omar G. Morales-Saavedra , K. Sanchez-Montes , M. Martínez-García , "Synthesis and NLO behavior of oligo(phenylenevinylene)-Porphyrin dendrimers", Dyes. Pigm. 96, 125-129, 2013.
D. Wang, T. Imae, "Fluorescence emission from dendrimers and its pH dependence", J. Am. Chem. Soc. 126, 13204-13205, 2004.
Miri, F., Gorji, S., & Panahi, F. (2018). Investigation of the Behavior of Conjugated Fluorescence Dyes as Amine Sensors. Journal of Studies in Color World, 8(3), 55-70.
MLA
Fateme Miri; Saeideh Gorji; Farhad Panahi. "Investigation of the Behavior of Conjugated Fluorescence Dyes as Amine Sensors". Journal of Studies in Color World, 8, 3, 2018, 55-70.
HARVARD
Miri, F., Gorji, S., Panahi, F. (2018). 'Investigation of the Behavior of Conjugated Fluorescence Dyes as Amine Sensors', Journal of Studies in Color World, 8(3), pp. 55-70.
VANCOUVER
Miri, F., Gorji, S., Panahi, F. Investigation of the Behavior of Conjugated Fluorescence Dyes as Amine Sensors. Journal of Studies in Color World, 2018; 8(3): 55-70.
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