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Effect of hydrophobic moiety on the gelation behavior of pyridyl boronic acid-derived amphiphiles: application in entrapment and release of vitamin B12

  • Sumita RoyEmail author
  • Monali Maiti
  • Siddhartha Das
  • Aparna Roy
Original Paper

Abstract

Low molecular weight organic gelators (LMOGs) have received great attention for their tremendous applications in multiple fields in the past few decades. Therefore, nowadays, synthesis of new type of LMOGs is a demanding field of research. In this work, the effect of hydrophobic moiety on gelation behavior of three synthesized pyridyl boronic acid-derived amphiphiles named sodium, 2-decylpyridine-5-boronate (SDPB), sodium, 2-oxydecylpyridine-5-boronate (SODPB) and sodium, 2-oxydodecylpyridine-5-boronate (SODDPB) has been investigated. The results confirmed that these amphiphiles are good gelators in common organic solvents in the presence of 60 μl of buffer solution and the gelation capability diminished in case of oxygen atom present in the alkyl chain. Further distortion of gelation process was observed with increase of chain length in oxy-alkyl chain. Rheological measurements established that the gel emulsion of SDPB is most stable towards external forces with highest elasticity value. XRD study was performed to analyze the orientation of the alkyl chain in the 3D network structure in the gel emulsions. The morphological changes with respect to concentration were investigated by FE-SEM study of the gel emulsions. The prepared gel emulsions with these amphiphiles are capable to entrap and release the biomolecule vitamin B12 at room temperature keeping the structure and activity unchanged which is indicative that the amphiphiles can be successfully utilized in pharmaceutical industries as drug delivery vehicles.

Highlights

  • Efficient single-chain pyridyl boronic acid gelators of organic solvents and mineral oils.

  • Decrease in gelation ability by the introduction of ether linkage in the hydrophobic part.

  • Concentration-dependent morphology change was observed.

  • Entrapment and release of biomolecule at room temperature.

Graphic abstract

Keywords

Boronic acid Amphiphile Gelator Entrapment Release Vitamin B12 

Notes

Acknowledgements

SD is thankful to UGC [20/12/2015(ii)EU-V] for his fellowship. AR acknowledges DST [SR/WOS-A/CS-41/2018(G)] for her fellowship. DST FIST and UGC SAP program of the department and instrumental facilities of USIC, Vidyasagar University, are acknowledged.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

11696_2019_865_MOESM1_ESM.doc (3 mb)
Supplementary material 1 (DOC 3070 kb)

References

  1. Akutagawa T, Kakiuchi K, Hasegawa T, Noro S, Nakamura T, Hasegawa H, Mashiko S, Becher J (2005) Molecularly assembled nanostructures of a redox-active organogelator. Angew Chem Int Ed 44:7283.  https://doi.org/10.1002/anie.200502336 CrossRefGoogle Scholar
  2. Amabilino DB, Smith DK, Steed JW (2017) Supramolecular materials. Chem Soc Rev 46:2404–2420.  https://doi.org/10.1039/c7cs00163k CrossRefGoogle Scholar
  3. Badami AS, Kreke MR, Thompson M, Riffle JS, Goldstein AS (2006) Effect of fiber diameter on spreading, proliferation, and differentiation of osteoblastic cells on electrospun poly (lactic acid) substrates. Biomaterials 27:596–606.  https://doi.org/10.1016/j.biomaterials.2005.05.084 CrossRefGoogle Scholar
  4. Ben AE, Cochereau R, Dechancé C, CapronI Nicolai T, Benyahia L (2018) Water-in-water emulsion gels stabilized by cellulose nanocrystals. Langmuir 34:6887–6893.  https://doi.org/10.1021/acs.langmuir.8b01239 CrossRefGoogle Scholar
  5. Bhattacharya S, Samanta SK (2016) Soft-nanocomposites of nanoparticles and nanocarbons with supramolecular and polymer gels and their applications. Chem Rev 116:11967–12028.  https://doi.org/10.1021/acs.chemrev.6b00221 CrossRefGoogle Scholar
  6. Binks BP (2002) Macroporous silica from solid-stabilized emulsion templates. Adv Mater 14:1824–1827.  https://doi.org/10.1002/adma.200290010 CrossRefGoogle Scholar
  7. Cai W, Wang CT, Xu YX, Jiang XK, Li ZT (2008) Vesicles and organogels from foldamers: a solvent-modulated self-assembling process. J Am Chem Soc 130:6936.  https://doi.org/10.1021/ja801618p CrossRefGoogle Scholar
  8. Caldero G, Llina’s M, Garcı’a-Celma MJ, Solans C (2010) Studies on controlled release of hydrophilic drugs from W/O high internal phase ratio emulsions. J Pharm Sci 99:701–711.  https://doi.org/10.1002/jps.21850 CrossRefGoogle Scholar
  9. Cameron NR (2005) High internal phase emulsion templating as a route to well-defined porous polymers. Polymer 46:1439–1449.  https://doi.org/10.1016/j.polymer.2004.11.097 CrossRefGoogle Scholar
  10. Cameron NR, Sherington DC (1996) High internal phase emulsions (HIPEs)—structure, properties and use in polymer preparation. Adv Polym Sci 126:163–214.  https://doi.org/10.1007/3-540-60484-7_4 CrossRefGoogle Scholar
  11. Capito RM, Azevedo HS, Velichko Y, Mata A, Stupp SI (2008) Self-assembly of large and small molecules into hierarchically ordered sacs and membranes. Science 319:1812–1816.  https://doi.org/10.1126/science.1154586 CrossRefGoogle Scholar
  12. Chakrabarty A, Maiti M, Miyagi K, Teramoto Y (2018) Gel emulsion based on amphiphilic block copolymer: a template to develop porous polymeric monolith for the efficient adsorption of volatile organic compounds. ACS Appl Nano Mater 1:1569–1578.  https://doi.org/10.1021/acsanm.8b00068 CrossRefGoogle Scholar
  13. Chen X, Liu K, He P, Zhang H, Fang Y (2012) Preparation of novel W/O gel-emulsions and their application in the preparation of low-density materials. Langmuir 28:9275–9281.  https://doi.org/10.1021/la300856h CrossRefGoogle Scholar
  14. Chiou NR, Epstein AJ (2005) Polyaniline nano fibers prepared by dilute polymerization. Adv Mater 17:1679–1683.  https://doi.org/10.1002/adma.200401000 CrossRefGoogle Scholar
  15. Dickinson E, Yamamoto Y (1996) Effect of lecithin on the viscoelastic properties of β-lactoglobulin-stabilized emulsion gels. Food Hydrocoll 10:301–307.  https://doi.org/10.1016/S0268-005X(96)80005-1 CrossRefGoogle Scholar
  16. Dong W, Cogbill A, Zhang T, Ghosh S, Tian ZR (2006) Multifunctional, catalytic nanowire membranes and the membrane-based 3D devices. J Phys Chem B 110:16819–16822.  https://doi.org/10.1021/jp0637633 CrossRefGoogle Scholar
  17. Dunstan TS, Fletcher PDI (2011) Compartmentalization and separation of aqueous reagents in the water droplets of water-in-oil high internal phase emulsions. Langmuir 27:3409–3415.  https://doi.org/10.1021/la200058d CrossRefGoogle Scholar
  18. Everett TA, Twite AA, Xie A, Battina SK, Hua DH, Higgins DA (2006) Preparation and characterization of nanofibrous perylene-diimide—polyelectrolyte composite thin films. Chem Mater 18:5937–5943.  https://doi.org/10.1021/cm061695r CrossRefGoogle Scholar
  19. Friggeri A, Feringa BL, van Esch J (2004) Entrapment and release of quinoline derivatives using a hydrogel of a low molecular weight gelator. J Controlled Release 97:241–248.  https://doi.org/10.1016/j.jconrel.2004.03.012 CrossRefGoogle Scholar
  20. Gao P, Zhan C, Liu M (2006) Controlled synthesis of double-and multiwall silver nanotubes with template organogel from a bolaamphiphile. Langmuir 22:775–779.  https://doi.org/10.1021/la0517787 CrossRefGoogle Scholar
  21. Gokmen MT, Camp WV, Colver PJ, Bon SAF, Du Prez FE (2009) Fabrication of porous “clickable” polymer beads and rods through generation of high internal phase emulsion (HIPE) droplets in a simple microfluidic device. Macro Mol 42:9289–9294.  https://doi.org/10.1021/ma9018679 CrossRefGoogle Scholar
  22. Grigoriou S, Johnson EK, Chen L, Adams DJ, James TD, Cameron PJ (2012) Dipeptide hydrogel formation triggered by boronic acid–sugar recognition. Soft Matter 8:6788–6791.  https://doi.org/10.1039/C2SM25713K CrossRefGoogle Scholar
  23. Huang YJ, Ouyang WJ, Wu X, Li ZFossey JS, James TD, Jiang YB (2013) Glucose sensing via aggregation and the use of “knock-out” binding to improve selectivity. J Am Chem Soc 135:1700–1703.  https://doi.org/10.1021/ja311442x CrossRefGoogle Scholar
  24. Ichinose I, Kurashima K, Kunitake T (2004) Spontaneous formation of cadmium hydroxide nanostrands in water. J Am Chem Soc 126:7162–7163.  https://doi.org/10.1021/ja049141h CrossRefGoogle Scholar
  25. Ikem VO, Menner A, Horozov TS, Bismarck A (2010) Highly permeable macroporous polymers synthesized from pickering medium and high internal phase emulsion templates. Adv Mater 22:3588–3592.  https://doi.org/10.1002/adma.201000729 CrossRefGoogle Scholar
  26. Ikem VO, Menner A, Bismarck A (2011) Tailoring the mechanical performance of highly permeable macroporous polymers synthesized via pickering emulsion templating. Soft Matter 7:6571–6577.  https://doi.org/10.1039/C1SM05272A CrossRefGoogle Scholar
  27. Imhof A, Pine DJ (1997) Ordered macroporous materials by emulsion templating. Nature 389:948–951.  https://doi.org/10.1038/40105 CrossRefGoogle Scholar
  28. Jung JH, Ono Y, Shinkai S (2000) Sol–gel polycondensation of tetraethoxysilane in a cholesterol-based organogel system results in chiral spiral silica. Angew Chem Int Ed 39:1862CrossRefGoogle Scholar
  29. Kang SH, Jung BM, Kim WJ, Chang JY (2008) Embedding nanofibers in a polymer matrix by polymerization of organogels comprising heterobifunctional organogelators and monomeric solvents. Chem Mater 20:5532.  https://doi.org/10.1021/cm800867b CrossRefGoogle Scholar
  30. Khatua D, Dey J (2005) Spontaneous formation of gel emulsions in organic solvents and commercial fuels induced by a novel class of amino acid derivatized surfactants. Langmuir 21:109–114.  https://doi.org/10.1021/la0481896 CrossRefGoogle Scholar
  31. Ki CS, Gang EH, Um IC, Park YH (2007) Nanofibrous membrane of wool keratose/silk fibroin blend for heavy metal ion adsorption. J Membr Sci 302:20–26.  https://doi.org/10.1016/j.memsci.2007.06.003 CrossRefGoogle Scholar
  32. Kim F, Kwan S, Akana J, Yang P (2001) Langmuir–blodgett nanorod assembly. J Am Chem Soc 123:4360–4361.  https://doi.org/10.1021/ja0059138 CrossRefGoogle Scholar
  33. Kobayashi H, Amaike M, Jung JH, Friggeri A, Shinkai S, Reinhoudt DN (2001) Organogel or polymer gel; facilitated gelation of a sugar-based organic gel by the addition of a boronic acid-appended polymer. Chem Commun 11:1038–1039.  https://doi.org/10.1039/b102436c CrossRefGoogle Scholar
  34. Ku CY, Nostro PL, Chen SH (1997) Structural study of the gel phase of a semifluorinated alkane in a mixed solvent. J Phys Chem B 101:908–914.  https://doi.org/10.1021/jp963120v CrossRefGoogle Scholar
  35. Li D, Frey MW, Baeumne AJ (2006a) Electrospun polylactic acid nanofiber membranes as substrates for biosensor assemblies. J Membr Sci 279:354–363.  https://doi.org/10.1016/j.memsci.2005.12.036 CrossRefGoogle Scholar
  36. Li D, Frey MW, Joo YL (2006b) Characterization of nanofibrous membranes with capillary flow porometry. J Membr Sci 286:104–114.  https://doi.org/10.1016/j.memsci.2006.09.020 CrossRefGoogle Scholar
  37. Li J, Zhang J, Zhao Y, Han B, Yang G (2012) High-internal-ionic liquid-phase emulsions. Chem Commun 48:994–996.  https://doi.org/10.1039/C2CC15922H CrossRefGoogle Scholar
  38. Lim HN, Kassim A, Huang NM, Khiewc PS, Chiu WS (2009) Three-dimensional flower-like brushite crystals prepared from high internal phase emulsion for drug delivery application. Coll Surf A 345:211–218.  https://doi.org/10.1016/j.colsurfa.2009.05.008 CrossRefGoogle Scholar
  39. Luo Y, Wang AN, Gao X (2012) Pushing the mechanical strength of PolyHIPEs up to the theoretical limit through living radical polymerization. Soft Matter 8:1824–1830.  https://doi.org/10.1039/C1SM06756G CrossRefGoogle Scholar
  40. Ma PX (2004) Scaffolds for tissue fabrication. Mater Today 7:30–40.  https://doi.org/10.1016/S1369-7021(04)00233-0 CrossRefGoogle Scholar
  41. Ma Z, Kotaki M, Inai R, Ramakrishna S (2005) Potential of nanofiber matrix as tissue-engineering scaffolds. Tissue Eng 11:101–109.  https://doi.org/10.1089/ten.2005.11.101 CrossRefGoogle Scholar
  42. Maeda H, Haketa Y, Nakanishi T (2007) Aryl-substituted C3-bridged oligopyrroles as anion receptors for formation of supramolecular organogels. J Am Chem Soc 129:13661.  https://doi.org/10.1021/ja074435z CrossRefGoogle Scholar
  43. Maiti M, Roy A, Roy S (2013) Effect of pH and oxygen atom of the hydrophobic chain on the self-assembly property and morphology of the pyridyl boronic acid based amphiphiles. Langmuir 29:13329–13338.  https://doi.org/10.1021/la403379g CrossRefGoogle Scholar
  44. Maiti M, Roy A, Roy S (2014) Effect of pH and amphiphile concentration on the gel-emulsion of sodium salt of 2-dodecylpyridine-5-boronic acid: entrapment and release of vitamin B12. Colloids and surfaces a: physicochem. Eng Aspects 461:76–84.  https://doi.org/10.1016/j.colsurfa.2014.07.030 CrossRefGoogle Scholar
  45. Maiti M, Roy A, Roy S (2016) Surface and self-organization of sodium salt of 2-decyl pyridine-5-boronic acid and sodium salt of 2-oxydecyl pyridine-5-boronic acid at two different pHs. Coll Polym Sci 294:171–179.  https://doi.org/10.1007/s00396-015-3760-z CrossRefGoogle Scholar
  46. Mayr J, Saldías C, Díaz Díaz D (2018) Release of small bioactive molecules from physical gels. Chem Soc Rev 47:1484–1515.  https://doi.org/10.1039/c7cs00515f CrossRefGoogle Scholar
  47. Mehwish N, Dou X, Zhao Y, Feng CL (2019) Supramolecular fluorescent hydrogelators as bio-imaging probes. Mater. Horiz. 6:14–44.  https://doi.org/10.1039/c8mh01130c CrossRefGoogle Scholar
  48. Miao Q, Chen X, Liu L, Peng J, Fang Y (2014) Synergetic effect based gel-emulsions and their utilization for the template preparation of porous polymeric monoliths. Langmuir 30:13680–13688.  https://doi.org/10.1021/la502988x CrossRefGoogle Scholar
  49. Mieden-Gundert G, Klein L, Fischer M, Vogtle F, Heuze K, Pozzo JL, Vallier M, Fages F (2001) Rational design of low molecular mass organogelators: toward a library of functional N-Acyl-1, ω-Amino acid derivatives. Angew Chem Int Ed 40:3164.  https://doi.org/10.1002/1521-3773 CrossRefGoogle Scholar
  50. Moy CL, Kaliappan R, McNeil AJ (2011) Aryl trihydroxyborate salts: thermally unstable species with unusual gelation abilities. J Org Chem 76:8501–8507.  https://doi.org/10.1021/jo201353j CrossRefGoogle Scholar
  51. Nadeem M, Rangkuti C, Anuar K, Haq MRU, Tan IB, Shah SS (2006) Diesel engine performance and emission evaluation using emulsified fuels stabilized by conventional and gemini surfactants. Fuel 85:2111–2119.  https://doi.org/10.1016/j.fuel.2006.03.013 CrossRefGoogle Scholar
  52. Namasivayam AM, Korakianitis T, Crookes RJ, BobManuel KDH, Olsen J (2010) Biodiesel, emulsified biodiesel and dimethyl ether as pilot fuels for natural gas fuelled engines. Appl Energy 87:769–778.  https://doi.org/10.1016/j.apenergy.2009.09.014 CrossRefGoogle Scholar
  53. Nostro PL, Ku CY, Chen SH, Lin JS (1995) Effect of a semifluorinated copolymer on the phase separation of a fluorocarbon/hydrocarbon mixture. J Phys Chem 99:10858–10864.  https://doi.org/10.1021/j100027a029 CrossRefGoogle Scholar
  54. Ogawa T, Ding B, Sone Y, Shiratori S (2007) Super-hydrophobic surfaces of layer-by-layer structured film-coated electrospun nanofibrous membranes. Nanotechnology 18:165607.  https://doi.org/10.1088/0957-4484/18/16/165607 CrossRefGoogle Scholar
  55. Oschatz M, Borchardt L, Thommes M, Cychosz KA, Senkovska I, Klein N, Frind R, Leistner M, Presser V, Gogotsi Y, Kaskel S (2012) Carbide-derived carbon monoliths with hierarchical pore architectures. Angew Chem Int Ed 51:7577–7580.  https://doi.org/10.1002/anie.201200024 CrossRefGoogle Scholar
  56. Pal A, Dey J (2011a) Water-induced physical gelation of organic solvents by N-(n-Alkylcarbamoyl)-l-alanine amphiphiles. Langmuir 27:3401–3408.  https://doi.org/10.1021/la105027b CrossRefGoogle Scholar
  57. Pal A, Dey J (2011b) Rheology and thermal stability of pH-dependent hydrogels of N-acyl-l-carnosine amphiphiles: effect of the alkoxy tail length. Soft Matter 7:10369–10376.  https://doi.org/10.1039/C1SM06209C CrossRefGoogle Scholar
  58. Patra T, Pal A, Dey J (2010) A Smart supramolecular hydrogel of Nα-(4-n-alkyloxybenzoyl)-l-histidine exhibiting pH-modulated properties. Langmuir 26:7761–7767.  https://doi.org/10.1021/la904540x CrossRefGoogle Scholar
  59. Peng X, Karan S, Ichinose I (2009) Ultrathin nanofibrous films prepared from cadmium hydroxide nanostrands and anionic surfactants. Langmuir 25:8514–8518.  https://doi.org/10.1021/la8040693 CrossRefGoogle Scholar
  60. Pettignano A, Grijalvo S, Häring M, Eritja R, Tanchoux N, Quignard F, DíazDíaz D (2017) Boronic acid-modified alginate enables direct formation of injectable, self-healing and multistimuli-responsive hydrogels. Chem Commun 53:3350–3353.  https://doi.org/10.1039/C7CC00765E CrossRefGoogle Scholar
  61. Podsiadlo P, Sui L, Elkasabi Y, Burgardt P, Lee J, Miryala A, Kusumaatmaja W, Carman MR, Shtein M, Kieffer J, Lahann J, Kotov NA (2007) Layer-by-layer assembled films of cellulose nanowires with antireflective properties. Langmuir 23:7901–7906.  https://doi.org/10.1021/la700772a CrossRefGoogle Scholar
  62. Roy A, Maiti M, Nayak R, Roy S (2013) Effect of amide hydrogen bonding on spontaneously formed gel-emulsions by two pyridyl carboxylic acid based amphiphiles, sodium salt of 2-dodecylpyridine-5-carboxylic acid and sodium salt of [2-dodecylpyridine-5-carboxylic]glycine: entrapment and release of vitamin B12. J Mater Chem B 1:5588.  https://doi.org/10.1039/C3TB20970A CrossRefGoogle Scholar
  63. Roy S, Maiti M, Roy A (2017) A new class of boronic acid-derived amphiphile-based gel emulsions capable of entrapping and releasing vitamin B12 and doxorubicin. Chem Sel 2:6929–6939.  https://doi.org/10.1002/slct.201701397 Google Scholar
  64. Roy A, Roy S, Pradhan A, MaitiChoudhury S, Nayak RR (2018) Gel-emulsion properties of nontoxic nicotinic acid-derived glucose sensor. Ind Eng Chem Res 57:2847–2855.  https://doi.org/10.1021/acs.iecr.7b04187 CrossRefGoogle Scholar
  65. Sawicka K, Gouma P, Simon S (2005) Electrospun biocomposite nanofibers for urea biosensing. Sens Actuators B 108:585–588CrossRefGoogle Scholar
  66. Sekitani T, Noguchi Y, Hata K, Fukushima T, Aida T, Someya T (2008) A rubberlike stretchable active matrix using elastic conductors. Science 321:1468–1472.  https://doi.org/10.1126/science.1160309 CrossRefGoogle Scholar
  67. Shirakawa M, Fujita N, Shinkai S (2005) A stable single piece of unimolecularly π-stacked porphyrin aggregate in a thixotropic low molecular weight gel: a one-dimensional molecular template for polydiacetylene wiring up to several tens of micrometers in length. J Am Chem Soc 127:4164–4165.  https://doi.org/10.1021/ja042869d CrossRefGoogle Scholar
  68. Silverstein MS (2014) Emulsion-templated porous polymers: a retrospective perspective. Polymer 55:304–320.  https://doi.org/10.1016/j.polymer.2013.08.068 CrossRefGoogle Scholar
  69. Sok Line VL, Remondetto GE, Subirade M (2005) Cold gelation of β-lactoglobulin oil-in-water emulsions. Food Hydrocoll 19:269–278.  https://doi.org/10.1016/j.foodhyd.2004.06.004 CrossRefGoogle Scholar
  70. Sugiyasu K, Fujita N, Shinkai S (2004) Visible-light-harvesting organogel composed of cholesterol-based perylene derivatives. Angew Chem Int Ed 43:1229.  https://doi.org/10.1002/anie.200352458 CrossRefGoogle Scholar
  71. Wu Z, Chen Z, Du X, Logan JM, Sippel J, Nikolou M, Kamaras K, Reynolds JR, Tanner DB, Hebard AF, Rinzler AG (2004) Transparent, conductive carbon nanotube films. Science 305:1273–1276.  https://doi.org/10.1126/science.1101243 CrossRefGoogle Scholar
  72. Yang P (2003) A centuries-old technique for transporting timber is the inspiration for a new method of assembling nanowires into large-scale, ordered patterns that could form the basis of a new generation of electronic devices. Nature 425:243–244.  https://doi.org/10.1038/425243a CrossRefGoogle Scholar
  73. Yang H, Yi T, Zhou ZG, Zhou YF, Wu JC, Xu M, Li FY, Huang CH (2007) Switchable fluorescent organogels and mesomorphic superstructure based on naphthalene derivatives. Langmuir 23:8224.  https://doi.org/10.1021/la7005919 CrossRefGoogle Scholar
  74. Yuan J, Liu X, Akbulut O, Hu J, Suib SL, Kong J, Stellacci F (2008) Superwetting nanowire membranes for selective absorption. Nat Nanotechnol 3:332–336.  https://doi.org/10.1038/nnano.2008.136 CrossRefGoogle Scholar
  75. Zhang W, Gao C (2017) Morphology transformation of self-assembled organic nanomaterials in aqueous solution induced by stimuli-triggered chemical structure changes. J Mater Chem A 5:16059–16104.  https://doi.org/10.1039/c7ta02038d CrossRefGoogle Scholar
  76. Zhang X, Du AJ, Lee P, Sun DD, Leckie JO (2008) TiO2 nanowire membrane for concurrent filtration and photocatalytic oxidation of humic acid in water. J Membr Sci 313:44–51.  https://doi.org/10.1016/j.memsci.2007.12.045 CrossRefGoogle Scholar
  77. Zhang B, Zhang J, Liu C, Peng L, Sang X, Han B, Ma X, Luo T, Tan X, Yang G (2016) High-internal-phase emulsions stabilized by metal-organic frameworks and derivation of ultralight metal-organic aerogels. Sci Rep 6:21401.  https://doi.org/10.1038/srep21401 CrossRefGoogle Scholar
  78. Zhou C, Gao W, Yang K, XLong U, Ding J, Chen J, Liu M, Huang X, Wang S, Wu H (2013) A novel glucose/pH responsive low-molecular-weight organogel of easy recycling. Langmuir 29:13568–13575.  https://doi.org/10.1021/la4033578 CrossRefGoogle Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2019

Authors and Affiliations

  • Sumita Roy
    • 1
    Email author
  • Monali Maiti
    • 1
  • Siddhartha Das
    • 1
  • Aparna Roy
    • 1
  1. 1.Department of Chemistry and Chemical TechnologyVidyasagar UniversityMidnaporeIndia

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