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Journal of Polymer Research

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01-04-2019 | ORIGINAL PAPER

Dual responsive spiropyran-ended poly(N-vinyl caprolactam) for reversible complexation with metal ions

Authors: Zhouxiaoshuang Yang, Feng Wang, Hui Liu

Published in: Journal of Polymer Research | Issue 4/2019

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Abstract

With the spiropyran-containing compound as the initiator, dual responsive spiropyran-ended poly(N-vinyl caprolactam) (SP-PNVCL) was synthesized by atom transfer radical polymerization. The structure of the resulting polymer was characterized by ¹H NMR and gel permeation chromatography, and the polymer had both reversible light-responsive and thermo-sensitive behaviors. Metal ions could be bound between merocyanine formed by photoisomerization of spiropyran and the amino group of N-vinyl caprolactam unit through synergetic coordination. The complexation of SP-PNVCL with several metal ions was investigated by UV-Vis absorption spectroscopy, and it was found that SP-PNVCL might be used as a potential recognition probe for Fe²⁺, accompanied by obvious color change from colorless to brown by naked eye. The detection limit and photo-reversible recyclable behaviors of SP-PNVCL for Fe²⁺ were also investigated in details. The kind of spiropyran-ended poly(N-vinyl caprolactam) had great application potential in environment protection and biological area.

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Sui BL, Tang SM, Liu TH, Kim BS, Belfield KD (2014) Novel BODIPY-based fluorescence turn-on sensor for Fe³⁺ and its bioimaging application in living cells. ACS Appl Mater Inter 6:18408–18412CrossRef

Kagit R, Yildirim M, Ozay O, Yesilot S, Ozay H (2014) Phosphazene based multicentered naked-eye fluorescent sensor with high selectivity for Fe³⁺ ions. Inorg Chem 53:2144–2151CrossRef

Santiago AA, Ibarra-Palos A, Cruz-Morales JA, Sierra JM, Abatal K (2018) Synthesis, characterization, and heavy metal adsorption properties of sulfonated aromatic polyamides. High Perform Polym 30:591–601CrossRef

Jia YY, Wang L, Ma L, Yang ZG (2018) Speciation analysis of six arsenic species in marketed shellfish: extraction optimization and health risk assessment. Food Chem 244:311–316CrossRef

Fu L, Shi SY, Chen XQ (2018) Accurate quantification of toxic elements in medicine food homologous plants using ICP-MS/MS. Food Chem 245:692–697CrossRef

Cui HQ, Liu H, Chen S, Wang RM (2015) Synthesis of amphiphilic spiropyran-based random copolymer by atom transfer radical polymerization for Co²⁺ recognition. Dyes Pigments 115:50–57CrossRef

Urek SK, Francic N, Turel M, Lobnik A (2013) Sensing heavy metals using mesoporous-based optical chemical sensors. J Nanomater:501320

Lechuga LM (2015) Optical biochemical and chemical sensors. Anal Bioanal Chem 404:2795–2796CrossRef

Hussein MA, Alam MM, Alenazi NA, Alamry KA, Asiri AM, Rahman MM (2018) Nanocomposite based functionalized Polyethersulfone and conjugated ternary ZnYCdO nanomaterials for the fabrication of selective Cd²⁺ sensor probe. J Polym Res 25:262CrossRef

10.

Ullah N, Mansha M, Khan I, Qurashi A (2018) Nanomaterial-based optical chemical sensors for the detection of heavy metals in water: recent advances and challenges. Trac-Trend Anal Chem 100:155–166CrossRef

11.

Otsuki J, Akasaka T, Araki K Molecular switches for electron and energy transfer processes based on metal complexes. Coordin. Chem. Rev 252:32–56CrossRef

12.

Wang F, Tang JT, Liu H, Yu GP, Zou YP (2019) Self-assembled polymeric micelles as amphiphilic particulate emulsifiers for controllable Pickering emulsions. Mater Chem Front 3:356–364CrossRef

13.

Wang F, Yu XY, Yang ZXS, Duan H, Zhang ZJ, Liu H (2018) Dual pH- and light-responsive amphiphilic random copolymer nanomicelles as particulate emulsifiers to stabilize the oil/water interface. J Phys Chem C 122:18995–19003CrossRef

14.

Wang F, Liu H (2018) Dual-functional emulsifying/antifogging coumarin-containing polymeric micelle. J Phys Chem C 122:3434–3442CrossRef

15.

Li LX, Lu B, Zhang Y, Xing XD, Wu XY, Liu ZL (2015) Multi-sensitive copolymer hydrogels of N-isopropylacrylamide with several polymerizable azobenzene-containing monomers. J Polym Res 22:176CrossRef

16.

Szymanski W, Beierle JM, Kistemaker HAV, Velema WA, Feringa BL (2013) Reversible photocontrol of biological systems by the incorporation of molecular photoswitches. Chem Rev 113:6114–6178CrossRef

17.

Bao LH, Sun JX, Li Q (2014) Synthesis and properties of waterborne polyurethane containing spiropyran groups. J Polym Res 21:575CrossRef

18.

Natali M, Aakeroey C, Desper J, Giordani S (2010) The role of metal ions and counterions in the switching behavior of a carboxylic acid functionalized spiropyran. Dalton T 39:8269–8277CrossRef

19.

Chernyshev AV, Voloshin NA, Metelitsa AV, Tkachev VV, Aldoshin SM, Solov'eva E, Rostovtseva I, Minkin VI (2013) Metal complexes of new photochromic chelator: structure, stability and photodissociation. J Photoch Photobio A 265:1–9CrossRef

20.

Paramonov SV, Lokshin V, Fedorova OA (2011) Spiropyran, chromene or spirooxazine ligands: insights into mutual relations between complexing and photochromic properties. J Photoch Photobio C 12:209–236CrossRef

21.

Suzuki T, Kawata Y, Kahata S, Kato T (2003) Photo-reversible Pb²⁺-complexation of insoluble poly(spiropyran methacrylate-co-perfluorohydroxy methacrylate) in polar solvents. Chem Commun (16):2004–2005

22.

Suzuki T, Hirahara Y, Bunya K, Shinozaki H (2010) Photo-reversible and selective Cu²⁺ complexation of a spiropyran-carrying sulfobetaine copolymer in saline solution. J Mater Chem 20:2773–2779CrossRef

23.

Fries K, Samanta S, Orski S, Locklin J (2008) Reversible colorimetric ion sensors based on surface initiated polymerization of photochromic polymers. Chem Commun (47):6288–6290

24.

Fries KH, Driskell JD, Samanta S, Locklin J (2010) Spectroscopic analysis of metal ion binding in spiropyran containing copolymer thin films. Anal Chem 82:3306–3314CrossRef

25.

Fries KH, Driskell JD, Sheppard GR, Locklin J (2011) Fabrication of spiropyran-containing thin film sensors used for the simultaneous identification of multiple metal ions. Langmuir 27:12253–12260CrossRef

26.

Fries KH, Sheppard GR, Bilbrey JA, Locklin J (2014) Tuning chelating groups and comonomers in spiropyran-containing copolymer thin films for color-specific metal ion binding. Polym Chem 5:2094–2102CrossRef

27.

Connal LA, Franks GV, Qiao GG (2010) Photochromic, metal-absorbing honeycomb structures. Langmuir 26:10397–10400CrossRef

28.

Dunne A, Delaney C, McKeon A, Nesterenko P, Paull B, Benito-Lopez F, Diamond D, Flores L (2018) Micro-capillary coatings based on spiropyran polymeric brushes for metal ion binding, detection, and release in continuous flow. Sensors 18:1083CrossRef

29.

Xie BQ, Qiu ZS, Huang WA, Cao J, Zhong HY (2013) Characterization and aqueous solution behavior of novel thermo-associating polymers. J Macromol Sci A 50:230–237CrossRef

30.

Cortez-Lemus NA, Licea-Claverie A (2016) Poly(N-vinylcaprolactam), a comprehensive review on a thermoresponsive polymer becoming popular. Prog Polym Sci 53:1–51CrossRef

31.

Mohammed MN, Bin Yusoh K, Shariffuddin JHBH (2018) Poly(N-vinyl caprolactam) thermoresponsive polymer in novel drug delivery systems: a review. Mater Express 8:21–34CrossRef

32.

Ventura C, Byrne R, Audouin F, Heise A (2011) Atom transfer radical polymerization synthesis and photoresponsive solution behavior of spiropyran end-functionalized polymers as simplistic molecular probes. J Polym Sci Pol Chem 49:3455–3463CrossRef

33.

Nakahara Y, Nakamura J, Shirotani N, Kimura K (2012) Synthesis of amphiphilic copolymers bearing a spirobenzopyran moiety at the end group and their photoresponsive micellar behaviors in water. Chem Lett 41:1142–1144CrossRef

34.

Shen HJ, Zhou M, Zhang Q, Keller A, Shen Y (2015) Zwitterionic light-responsive polymeric micelles for controlled drug delivery. Colloid Polym Sci 293:1685–1694CrossRef

35.

Wang F, Xu WS, Ouyang YS, Zhang LL, Liu H (2018) Reversible crosslinking terpolymer shell-based mesoporous silica nanoparticles as on-off nanocarriers for pyrene-releasing application. J Taiwan Inst Chem E 91:578–587CrossRef

36.

Zakharova MI, Coudret C, Pimienta V, Micheau JC, Sliwa M, Poizat O, Buntinx G, Delbaere S, Vermeersch G, Metelitsa AV, Voloshin N, Minkin VI (2011) Kinetic modelling of the photochromism and metal complexation of a spiropyran dye: application to the co(II)-spiroindoline-diphenyloxazolebenzopyran system. Dyes Pigments 89:324–329CrossRef

37.

Shiraishi Y, Matsunaga Y, Hirai T (2012) Selective colorimetric sensing of co(II) in aqueous media with a spiropyran-amide-dipicolylamine linkage under UV irradiation. Chem Commun 48:5485–5487CrossRef

38.

Sahoo PR, Kumar S (2016) Synthesis of an optically switchable salicylaldimine substituted naphthopyran for selective and reversible Cu²⁺ recognition in aqueous solution. RSC Adv 6:20145–20154CrossRef

39.

Heng S, McDevitt CA, Stubing DB, Whittall JJ, Thompson JG, Engler TK, Abell AD, Monro TM (2013) Microstructured optical fibers and live cells: a water-soluble, photochromic zinc sensor. Biomacromolecules 14:3376–3379CrossRef

40.

Banerjee A, Sahana A, Guha S, Lohar S, Hauli I, Mukhopadhyay SK, Matalobos JS, Das D (2012) Nickel(II)-induced excimer formation of a naphthalene-based fluorescent probe for living cell imaging. Inorg Chem 51:5699–5704CrossRef

41.

Han SL, Chen Y (2011) Mercury ion induced activation of the C-O bond in a photo-responsive spiropyran. Dyes Pigments 88:235–239CrossRef

42.

Bing QJ, Wang L, Li DL, Wang G (2018) A new high selective and sensitive turn-on fluorescent and ratiometric absorption chemosensor for Cu²⁺ based on benzimidazole in aqueous solution and its application in live cell. Spectrochim Acta A 202:305–313CrossRef

43.

Qi Y, Zhao J, Weng GJ, Li JJ, Zhu J, Zhao JW (2018) Modification-free colorimetric and visual detection of Hg²⁺ based on the etching from core-shell structural au-ag nanorods to nanorices. Sensor Actuat B-Chem 267:181–190CrossRef

44.

Choodum A, Sriprom W, Wongniramaikul W (2019) Portable and selective colorimetric film and digital image colorimetry for detection of iron. Spectrochim Acta A 208:40–47CrossRef

45.

Najarzadekan H, Sereshti H (2018) Transparent polycaprolactam electrospun nanofibers doped with 1,10-phenanthroline optical sensor for colorimetric determination of iron (II) and vitamin C. Fiber Polym 19:2149–2156CrossRef

Title: Dual responsive spiropyran-ended poly(N-vinyl caprolactam) for reversible complexation with metal ions
Authors: Zhouxiaoshuang Yang
Feng Wang
Hui Liu
Publication date: 01-04-2019
Publisher: Springer Netherlands
Published in: Journal of Polymer Research / Issue 4/2019
Print ISSN: 1022-9760
Electronic ISSN: 1572-8935
DOI: https://doi.org/10.1007/s10965-019-1747-z

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