Abstract
It was recently reported that, besides UV irradiated polymerization, polymerization of diacetylene compounds could also been initiated by radicals generated from enzyme catalyzed hydrogen peroxide (H2O2) decomposition. A new optical sensing method for H2O2 was proposed based on this phenomenon. However, the sensitivity of this method is relatively lower than existed ones. In the present work, phenylboronic acid (PBA) functionalized 10, 12-pentacosadiynoic acid (PDA-PBA) was synthesized and its vesicles were formed successfully as colorimetric sensor for H2O2 detection. It was found that color change during the polymerization of vesicles composed of the PBA modified monomer is much stronger than that of the non-modified one. The response of PDA-PBA vesicles to H2O2 is 16 times more sensitive than that of the PDA. The absorption of PDA-PBA at 650 nm is linearly related to the concentration of H2O2 and a detection limit of ~5 μM could be achieved.
Similar content being viewed by others
References
Petlicki J, Palusova D, van de Ven TGM (2005) Physicochemical aspects of catalytic decomposition of hydrogen peroxide by manganese compounds. Ind Eng Chem Res 44:2002–2010. doi:10.1021/ie049595n
Root R, Metcalf J, Oshino N, Chance B (1975) H2O2 release from human granulocytes during phagocytosis. I. documentation, quantitation, and some regulating factors. J Clin Investig 55:945–955. doi:10.1172/JCI108024
Stuart A. G. Evans, Joanne M. Elliott, Lynn M. Andrews, Philip N. Bartlett et al (2002) Detection of hydrogen peroxide at mesoporous platinum microelectrodes. Anal Chem 74: 1322–1326. doi:10.1021/ac011052p
Lei C-X, Hu S-Q, Shen G-L, Yu R-Q (2003) Immobilization of horseradish peroxidase to a nano-Au monolayer modified chitosan-entrapped carbon paste electrode for the detection of hydrogen peroxide. Talanta 59:981–988. doi:10.1016/S0039-9140(02)00641-0
He S, Shi W, Zhang X, Li J, et al (2010) β-cyclodextrins-based inclusion complexes of CoFe2O4 magnetic nanoparticles as catalyst for the luminol chemiluminescence system and their applications in hydrogen peroxide detection. Talanta 82:377–383. doi:10.1016/j.talanta.2010.04.055
Han JH, Jang J, Kim BK, Choi HN, et al (2011) Detection of hydrogen peroxide with luminol electrogenerated chemiluminescence at mesoporous platinum electrode in neutral aqueous solution. J Electroanal Chem 660:101–107. doi:10.1016/j.jelechem.2011.06.012
Pajor-Swierzy A, Kolasinska-Sojka M, Warszynski P (2014) The electroactive multilayer films of polyelectrolytes and Prussian blue nanoparticles and their application for H2O2 sensors. Colloid Polym Sci 292:455–465. doi:10.1007/s00396-013-3091-x
Fan J, Bian X, Niu Y, Bai Y, et al (2013) Formation of three-dimensional Nano-porous silver films and application toward electrochemical detection of hydrogen peroxide. Appl Surf Sci 285:185–189. doi:10.1016/j.apsusc.2013.08.034
Rismetov B, Ivandini TA, Saepudin E, Einaga Y (2014) Electrochemical detection of hydrogen peroxide at platinum-modified diamond electrodes for an application in melamine strip tests. Diam Relat Mater 48:88–95. doi:10.1016/j.diamond.2014.07.003
Nakashima K, Wada M, Kuroda N, Akiyama S, et al (1994) High-performance liquid chromatographic determination of hydrogen peroxide with peroxyoxalate chemiluminescence detection. J Liq Chromatogr 17:2111–2126. doi:10.1080/10826079408013535
Shiang YC, Huang CC, Chang HT (2009) Gold nanodot-based luminescent sensor for the detection of hydrogen peroxide and glucose. Chem Commun 23:3437–3439. doi:10.1039/b901916b
Kim JM, Lee YB, Yang DH, et al (2005) A polydiacetylene-based fluorescent sensor chip. J Am Chem Soc 127:17580–17581. doi:10.1021/ja0547275
Kolusheva S, Molt O, Herm M, et al (2005) Selective detection of catecholamines by synthetic receptors embedded in chromatic polydiacetylene vesicles. J Am Chem Soc 127:10000–10001. doi:10.1021/ja052436q
Wu A, Yuan G, Tian H, Federici JF, et al (2014) Effect of alkyl chain length on chemical sensing of polydiacetylene and polydiacetylene/ZnO nanocomposites. Colloid Polym Sci 292:3137–3146. doi:10.1007/s00396-014-3365-y
Pecher J, Mecking S (2010) Nanoparticles of conjugated polymers. Chem Rev 110:6260–6279. doi:10.1021/cr100132y
Song YJ, Wei WL, Qu XG (2011) Colorimetric biosensing using smart materials. Adv Mater 23:4215–4236. doi:10.1002/adma.201101853
Lu S, Jia C, Duan X, Zhang X, et al (2014) Polydiacetylene vesicles for hydrogen peroxide detection. Colloid Surf A 443:488–491. doi:10.1016/j.colsurfa.2013.11.029
Wen F, Dong YH, Feng L, Wang S, et al (2011) Horseradish peroxidase functionalized fluorescent gold nanoclusters for hydrogen peroxide sensing. Anal Chem 83:1193–1196. doi:10.1021/ac1031447
Wu P, Cai Z, Chen J, Zhang H, et al (2011) Electrochemical measurement of the flux of hydrogen peroxide releasing from RAW 264.7 macrophage cells based on enzyme-attapulgite clay nanohybrids. Biosens Bioelectron 26:4012–4017. doi:10.1016/j.bios.2011.03.018
Tahir MN, André R, Sahoo JK, Jochum FD, et al (2011) Hydrogen peroxide sensors for cellular imaging based on horse radish peroxidase reconstituted on polymer-functionalized TiO2 nanorods. Nanoscale 3:3907–3914. doi:10.1039/c1nr10587f
Jonas U, Shah K, Norvez S, et al (1999) Reversible color switching and unusual solution polymerization of hydrazide-modified diacetylene lipids. J Am Chem Soc 121:4580–4588. doi:10.1021/ja984190d
Niwa M, Shibahara S, Higashi N (2000) Diacetylenic monolayers containing a boronic acid moiety form a chemically and thermally stable poly(diacetylene) film on water. J Mater Chem 10:2647–2651. doi:10.1039/b004371k
Lee J, Yarimaga O, Lee CH, Choi YK, et al (2011) Network polydiacetylene films: preparation, patterning, and sensor applications. Adv Funct Mater 21:1032–1039. doi:10.1002/adfm.201002042
Reppy MA, Pindzola BA (2007) Biosensing with polydiacetylene materials: structures, optical properties and applications. Chem Commun 14(42):4317–4338. doi:10.1039/b703691d
Evrard D, Touitou E, Kolusheva S, Fishov Y, et al (2001) A new colorimetric assay for studying and rapid screening of membrane penetration enhancers. Pharm Res 18:943–949. doi:10.1023/A:1010980009823
Su Y, Li J, Jiang L (2004) Effect of amphiphilic molecules upon chromatic transitions of polydiacetylene vesicles in aqueous solutions. Colloids Surf B: Biointerfaces 39:113–118. doi:10.1016/j.colsurfb.2003.12.005
Lee J, Jeong EJ, Kim J (2011) Selective and sensitive detection of melamine by intra/inter liposomal interaction of polydiacetylene liposomes. Chem Commun 47:358–360. doi:10.1039/c0cc02183k
Lee SW, Kang CD, Yang DH, et al (2007) The development of a generic bioanalytical matrix using polydiacetylenes. Adv Funct Mater 17:2038–2044. doi:10.1002/adfm.200600398
Guo CX, Boullanger P, Liu T, Jiang L (2005) Size effect of polydiacetylene vesicles functionalized with glycolipids on their colorimetric detection ability. J Phys Chem B 109:18765–18771. doi:10.1021/jp052580y
Schneider HJ, Tianjun L, Lomadze N (2004) Sensitivity increase in molecular recognition by decrease of the sensing particle size and by increase of the receptor binding site - a case with chemomechanical polymers. Chem Commun 21:2436–2437. doi:10.1039/b409331c
Acknowledgments
This work was supported by the National Science Foundation for Distinguished Young Scholars of China (No.21225626) and the Key Program of the National Natural Science Foundation of China (No.20936002).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Jia, C., Tang, J., Lu, S. et al. Enhanced Sensitivity for Hydrogen Peroxide Detection: Polydiacetylene Vesicles with Phenylboronic Acid Head Group. J Fluoresc 26, 121–127 (2016). https://doi.org/10.1007/s10895-015-1691-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-015-1691-1