Abstract
A practical fluorescent test dipstick for an efficient recognition of ammonia and amines vapors was developed. The prepared testing strip was based on a composite of molecularly imprinted chitosan nanoparticles, supported on cellulose paper assay, with artificial fluorescent receptor sites for ammonia/amines recognition in aqueous and gaseous phases. A modified chitosan nanoparticles containing fluorescein molecules, were successfully prepared and employed on cellulose paper strip creating fluorescent cellulose (FL-Cell) to act as “turn-on” fluorescent sensor for sensing and determining ammonia and organic amine vapor. We employed chitosan nanoparticles that had fluorescein incorporated as the fluorescent probe molecule, with a readout limit achieved for aqueous ammonia as low as 280 ppm at room temperature and atmospheric pressure. The sensor responded linearly relying on the aqueous ammonia concentration in the range of 0.13–280 ppm. The chromogenic fluorescent cellulose platform response depended on the acid-base characteristic effects of the fluorescein probe. The protonated form of fluorescein molecules immobilized within the chitosan nanoparticles were in a nanoenvironment demonstrating only weak fluorescence. When binding to ammonia/amine vapor, the fluorescein active sites were deprotonated and exhibited higher “turned-on” fluorescence as a result of exposure to those alkaline species. The simple fabrication and abovementioned characteristics of such fluorescent chitosan nanoparticles are such that they should be applicable for monitoring of ammonia/amines in either aqueous or vapor states. We studied the distribution of the fluorescent chitosan onto paper sheets fabricated from bleached bagasse pulp and coated with two different thicknesses of a fluorescent nanochitosan and blank nanochitosan solutions. A thin fluorescent nanochitosan layer was created on the surface of cellulose strips using an applicator. Its distribution was assessed by scanning electron microscopic (SEM) and transmission electron microscopic (TEM) analysis as well as Fourier-transform infrared spectroscopic (FT-IR) measurements. The mechanical properties were also tested. The exploitation of this “turn-on” fluorescence sensor invented platform should be amenable to different situations where determination of ammonia/amine vapor or aqueous solution is required.
Similar content being viewed by others
References
Stratton JE, Hutkins RW, Taylor SL (1991) Biogenic amines in cheese and other fermented foods: a review. J Food Prot 54(6):460–470
Khattab TA, Rehan M, Aly SA, Hamouda T, Haggag KM, Klapotke TM (2017) Fabrication of PAN-TCF-hydrazone nanofibers by solution blowing spinning technique: naked-eye colorimetric sensor. J Environ Chem Eng 5(3):2515–2523
Onal A (2007) A review: current analytical methods for the determination of biogenic amines in foods. Food Chem 103(4):1475–1486
Khattab TA, Tiu BDB, Adas S, Bunge SD, Advincula RC (2016) Solvatochromic, thermochromic and pH-sensory DCDHF-hydrazone molecular switch: response to alkaline analytes. RSC Adv 6(104):102296–102305
Li L, Gao P, Baumgarten M, Mullen K, Lu N, Fuchs H, Chi L (2013) High performance field-effect ammonia sensors based on a structured ultrathin organic semiconductor film. Adv Mater 25(25):3419–3425
Khattab TA (2018) Novel solvatochromic and halochromic sulfahydrazone molecular switch. J Mol Struct 1169:96–102
Abou-Yousef H, Khattab TA, Youssef YA, Al-Balakocy N, Kamel S (2017) Novel cellulose-based halochromic test strips for naked-eye detection of alkaline vapors and analytes. Talanta 170:137–145
Khattab TA, Gaffer HE (2016) Synthesis and application of novel tricyanofuran hydrazone dyes as sensors for detection of microbes. Color Technol 132(6):460–465
Thakur VK, Thakur MK (2014) Processing and characterization of natural cellulose fibers/thermoset polymer composites. Carbohydr Polym 109:102–117
de Oliveira Barud HG, da Silva RR, da Silva Barud H, Tercjak A, Gutierrez J, Lustri WR, de Oliveira Junior OB, Ribeiro SJL (2016) A multipurpose natural and renewable polymer in medical applications: bacterial cellulose. Carbohydr Polym 153:406–420
Kumar MNVR (2000) A review of chitin and chitosan applications. React Funct Polym 46(1):1–27
Francis Suh J-K, Matthew HWT (2000) Application of chitosan-based polysaccharide biomaterials in cartilage tissue engineering: a review. Biomaterials 21(24):2589–2598
Ngah WW, Teong LC, Hanafiah MAKM (2011) Adsorption of dyes and heavy metal ions by chitosan composites: a review. Carbohydr Polym 83(4):1446–1456
Kong M, Chen XG, Xing K, Park HJ (2010) Antimicrobial properties of chitosan and mode of action: a state of the art review. Int J Food Microbiol 144(1):51–63
Thakur VK, Voicu SL (2016) Recent advances in cellulose and chitosan based membranes for water purification: a concise review. Carbohydr Polym 146:148–165
Xu D, Qiu J, Wang Y, Yan J, Liu G-S, Yang B-R (2017) Chitosan-assisted buffer layer incorporated with hydroxypropyl methylcellulose-coated silver nanowires for paper-based sensors. Appl Phys Express 10(6):065002
Luo Y, Teng Z, Li Y, Wang Q (2015) Solid lipid nanoparticles for oral drug delivery: chitosan coating improves stability, controlled delivery, mucoadhesion and cellular uptake. Carbohydr Polym 122:221–229
Mansur AAP, Mansur HS (2015) Quantum dot/glycol chitosan fluorescent nanoconjugates. Nanoscale Res Lett 10(1):172
Geng Z, Zhang H, Xiong Q, Zhang Y, Zhao H, Wang G (2015) A fluorescent chitosan hydrogel detection platform for the sensitive and selective determination of trace mercury (II) in water. J Mater Chem A 3(38):19455–19460
Barata JFB, Pinto RJB, Vaz Serra VIRC, Silvestre AJD, Trindade T, Neves MGPMS, Cavaleiro JAS, Daina S, Sadocco P, Freire CSR (2016) Fluorescent bioactive corrole grafted-chitosan films. Biomacromolecules 17(4):1395–1403
Li Y, Liu Z, Zhu W, Fu H, Ding Y, Xie J, Yang W, Li L, Cheng C (2015) Two different emission-wavelength fluorescent probes for aluminum ion based on tunable fluorophores in aqueous media. J Fluoresc 25(3):603–611
Seema H, Shirinfar B, Shi G, Youn S, Ahmed N (2017) Facile synthesis of a selective biomolecule Chemosensor and fabrication of its highly fluorescent graphene complex. J Phys Chem B 121(19):5007–5016
Dong JX, Gao ZF, Zhang Y, Li BL, Li NB, Luo HQ (2017) A selective and sensitive optical sensor for dissolved ammonia detection via agglomeration of fluorescent ag nanoclusters and temperature gradient headspace single drop microextraction. Biosens Bioelectron 91:155–161
Schaude C, Meindl C, Frohlich E, Attard J, Mohr GJ (2017) Developing a sensor layer for the optical detection of amines during food spoilage. Talanta 170:481–487
El-Sherbiny IM, Hefnawy A, Salih E (2016) New core–shell hyperbranched chitosan-based nanoparticles as optical sensor for ammonia detection. Int J Biol Macromol 86:782–788
Khairy GM, Azab HA, El-Korashy SA, Steiner M-S, Duerkop A (2016) Validation of a fluorescence sensor Microtiterplate for biogenic amines in meat and cheese. J Fluoresc 26(5):1905–1916
Chen Y, Zhu C, Cen J, Bai Y, He W, Guo Z (2015) Ratiometric detection of pH fluctuation in mitochondria with a new fluorescein/cyanine hybrid sensor. Chem Sci 6(5):3187–3194
Jiao Y, Liu X, Zhou L, He H, Zhou P, Duan C, Peng X (2018) A fluorescein derivative-based fluorescent sensor for selective recognition of copper (II) ions. J Photochem Photobiol A Chem 355:67–71
Bao X, Cao Q, Wu X, Shu H, Zhou B, Geng Y, Zhu J (2016) Design and synthesis of a new selective fluorescent chemical sensor for Cu2+ based on a pyrrole moiety and a fluorescein conjugate. Tetrahedron Lett 57(8):942–948
Warratz R (2016) Electrochemical gas sensor with an ionic liquid as electrolyte for the detection of ammonia and amines. US Patent 9:395,323
Mirmohseni A, Oladegaragoze A (2003) Construction of a sensor for determination of ammonia and aliphatic amines using polyvinylpyrrolidone coated quartz crystal microbalance. Sensors Actuators B Chem 89(1–2):164–172
Crowley K, Morrin A, Hernandez A, O’Malley E, Whitten PG, Wallace GG, Smyth MR, Killard AJ (2008) Fabrication of an ammonia gas sensor using inkjet-printed polyaniline nanoparticles. Talanta 77(2):710–717
Hanson DR, McMurry PH, Jiang J, Tanner D, Huey LG (2011) Ambient pressure proton transfer mass spectrometry: detection of amines and ammonia. Environ Sci Technol 45(20):8881–8888
Diaz YJ, Page ZA, Knight AS, Treat NJ, Hemmer JR, Hawker CJ, de Alaniz JR (2017) A versatile and highly selective colorimetric sensor for the detection of amines. Chem Eur J 23(15):3562–3566
Huang X, Hu N, Gao R, Yu Y, Wang Y, Yang Z, Kong ESW, Wei H, Zhang Y (2012) Reduced graphene oxide-polyaniline hybrid: preparation, characterization and its applications for ammonia gas sensing. J Mater Chem 22(42):22488–22495
Takagai Y, Nojiri Y, Takase T, Hinze WL, Butsugan M, Igarashi S (2010) “Turn-on” fluorescent polymeric microparticle sensors for the determination of ammonia and amines in the vapor state. Analyst 135(6):1417–1425
Saharan V, Sharma G, Yadav M, Choudhary MK, Sharma SS, Pal A, Raliya R, Biswas P (2015) Synthesis and in vitro antifungal efficacy of cu–chitosan nanoparticles against pathogenic fungi of tomato. Int J Biol Macromol 75:346–353
Deng X, Cao M, Zhang J, Hu K, Yin Z, Zhou Z, Xiao X, Yang Y, Sheng W, Wu Y, Zeng Y (2014) Hyaluronic acid-chitosan nanoparticles for co-delivery of MiR-34a and doxorubicin in therapy against triple negative breast cancer. Biomaterials 35(14):4333–4344
Armarego WLF, Chai CLL (2013) Purification of laboratory chemicals. Butterworth-Heinemann
Lide DR (2004) CRC handbook of chemistry and physics 2004–2005: a ready-reference book of chemical and physical data
March J (1992) Advanced organic chemistry: reactions, mechanisms, and structure. John Wiley & Sons
Albert A (2012) The determination of ionization constants: a laboratory manual. Springer Science & Business Media
Perrin DD (1972) Dissociation constants of organic bases in aqueous solution: supplement 1972. Butterworths
Widmer S, Dorrestijn M, Camerlo A, Urek SK, Lobnik A, Housecroft CE, Constable EC, Scherer LJ (2014) Coumarin meets fluorescein: a Förster resonance energy transfer enhanced optical ammonia gas sensor. Analyst 139(17):4335–4342
Preininger C, Ludwig M, Mohr GJ (1998) Effect of the sol-gel matrix on the performance of ammonia fluorosensors based on energy transfer. J Fluoresc 8(3):199–205
Cao L-W, Wang H, Li J-S, Zhang H-S (2005) 6-oxy-(N-succinimidyl acetate)-9-(2′-methoxycarbonyl) fluorescein as a new fluorescent labeling reagent for aliphatic amines in environmental and food samples using high-performance liquid chromatography. J Chromatogr A 1063(1–2):143–151
Cao L, Wang H, Ma M, Zhang H (2006) Determination of biogenic amines in HeLa cell lysate by 6-oxy-(N-succinimidyl acetate)-9-(2′–methoxycarbonyl) fluorescein and micellar electrokinetic capillary chromatography with laser-induced fluorescence detection. Electrophoresis 27(4):827–836
Acknowledgements
The authors sincerely acknowledge the National Research Center of Egypt for financial support of this research activity under grant number 11090110.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of Interest
None.
Additional information
Publisher’s Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Khattab, T.A., Kassem, N.F., Adel, A.M. et al. Optical Recognition of Ammonia and Amine Vapor Using “Turn-on” Fluorescent Chitosan Nanoparticles Imprinted on Cellulose Strips. J Fluoresc 29, 693–702 (2019). https://doi.org/10.1007/s10895-019-02381-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-019-02381-5