Skip to main content
SpringerLink
Log in

Carbon-based nanocatalyst: An efficient and recyclable heterogeneous catalyst for one-pot synthesis of gem-bisamides, hexahydroacridine-1,8-diones and 1,8-dioxo-octahydroxanthenes

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

In this abstract, we discuss the progress related to sulfonated carbon-based materials in various acid-catalyzed organic transformations which are then further utilized in medicinal field, laboratories and industries. A simple and novel methodology was employed to prepare carbon-based nanocatalyst, i.e. cellulose[2-(sulfooxy)ethyl]mercaptosulfonic acid as a solid acid catalyst. This nanocatalyst is recyclable and also exhibited very high activity. Novel carbon-based nanocatalyst, i.e. cellulose[2-(sulfooxy)ethyl]mercaptosulfonic acid[SEMSA] was successfully synthesized by reacting mercaptoethanol and chlorosulfonic acid, and the catalytic activity of the prepared catalysts was evaluated for the one-pot synthesis of gem-bisamides from various aldehydes and benzamide, hexahydroacridine-1,8-diones via three-component condensation of aromatic aldehyde, dimedone and ammonium acetate or aromatic amine and 1,8-dioxo-octahydroxanthenes using aldehyde and dimedone. Application of this new heterogeneous nanocatalyst system offered the advantages of high yields, short reaction times, eco-friendly nature and easy work-up procedure compared to the conventional methods of the synthesis, and confirmation of products synthesized has been done using studies like 1H NMR and 13C NMR. Among the various catalysts, this nanocatalyst, i.e. cellulose [2-(sulfooxy)ethyl]mercaptosulfonic acid[SEMSA], was found to be the most active and selective and could be recycled several times without significant loss of activity. Also, scanning electron microscopy and transmission electron microscopy of the catalyst have been performed to know the internal and external morphology, size, thermo-gravimetric analysis to study the thermal stability and Fourier transform infrared spectroscopy to study the modification pattern of the catalyst have been undertaken and presented in this work. Due to its simple and inexpensive solid support, i.e. cellulose and environmentally benign toluene, ethanol and acetonitrile as solvents in three different transformations which are less toxic, easily available and less expensive than other solvents.

Graphic abstract

We reported here a novel route for the synthesis of gem-bisamides, hexahydroacridine-1,8-diones and 1,8-dioxo-octahydroxanthenes

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13

Similar content being viewed by others

References

  1. G. Kour, M. Gupta, Dalton Trans. 46, 7039 (2017)

    CAS  PubMed  Google Scholar 

  2. J.H. Clark, Pure Appl. Chem. 73, 103–111 (2001)

    CAS  Google Scholar 

  3. J.A. Melero, R. Grieken, G. Morales, Chem. Rev. 106, 3790–3812 (2006)

    CAS  PubMed  Google Scholar 

  4. S. Pathak, K. Debnath, A. Pramanik, Beilstein J. Org. Chem. 9, 2344–2353 (2013)

    PubMed  PubMed Central  Google Scholar 

  5. M. Kour, S. Paul, New J. Chem. 39, 6338–6350 (2015)

    CAS  Google Scholar 

  6. J. Cybulski, M. Cybulski, M. Sharma, R.A. Sheldon, Fine Chemicals Manufacture: Technology and Engineering, 1st edn. (Elsevier, Amsterdam, 2001)

    Google Scholar 

  7. D.M. Pore, U.V. Desai, T.S. Thopate, P.P. Wadgaonka, Synth. Commun. 34, 2135–2142 (2004)

    CAS  Google Scholar 

  8. A.D. Sagar, S.N. Chamle, M.V. Yadav, J. Chem. Pharm. Res. 5, 156–160 (2013)

    CAS  Google Scholar 

  9. J.H. Clark, Acc. Chem. Res. 35, 791–797 (2002)

    CAS  PubMed  Google Scholar 

  10. M.R. Mohammadizadeh, A. Hasaninejad, M. Bahramzadeh, Z.S. Khanjarlu, Synth. Commun. 39, 1152–1165 (2009)

    CAS  Google Scholar 

  11. S.N. Sadat, F. Hatamjafari, Orient. J. Chem. 31, 1191–1193 (2015)

    CAS  Google Scholar 

  12. A. Maleki, M. Kamalzare, Tetrahedron Lett. 55, 6931–6934 (2014)

    CAS  Google Scholar 

  13. A. Maleki, H. Movahed, P. Ravaghi, T. Kari, RSC Adv. 6, 98777–98787 (2016)

    CAS  Google Scholar 

  14. A. Maleki, M. Aghaei, R. Paydar, J. Iran. Chem. Soc. 14, 485–490 (2017)

    CAS  Google Scholar 

  15. A. Maleki, P. Ravaghi, M. Aghaei, H. Movahed, Res. Chem. Intermed. 43, 5485–5494 (2017)

    CAS  Google Scholar 

  16. A. Maleki, H. Movahed, P. Ravaghi, Carbohydr. Polym. 156, 259–267 (2017)

    CAS  PubMed  Google Scholar 

  17. A. Maleki, A.A. Jafari, S. Yousefi, Carbohydr. Polym. 175, 409–416 (2017)

    CAS  PubMed  Google Scholar 

  18. A. Maleki, P. Ravaghi, H. Movahed, Micro Nano Lett. 13, 591–594 (2018)

    CAS  Google Scholar 

  19. A. Maleki, Ultrason. Sonochem. 40, 460–464 (2017)

    PubMed  Google Scholar 

  20. A. Maleki, V. Eskandarpour, J. Rahimi, N. Hamidi, Carbohydr. Polym. 208, 251–260 (2018)

    PubMed  Google Scholar 

  21. W.J. Lee, U.N. Maiti, J.M. Lee, J. Lim, T.H. Han, S.O. Kim, Chem. Commun. 50, 6818–6830 (2014)

    CAS  Google Scholar 

  22. M. Okamura, A. Takagaki, M. Toda, J.N. Kondo, K. Domen, T. Tatsumi, M. Hara, S. Hayashi, Chem. Mater. 18, 3039–3045 (2006)

    CAS  Google Scholar 

  23. M. Toda, A. Takagaki, M. Okamura, J.N. Kondo, S. Hayashi, K. Hayashi, M. Hara, Nature 438, 178 (2005)

    CAS  PubMed  Google Scholar 

  24. A. Takagaki, M. Takagaki, M. Okamura, J.N. Kondo, S. Hayashi, K. Domen, M. Hara, Catal. Today 116, 157–161 (2006)

    CAS  Google Scholar 

  25. S. Suganuma, K. Nakajima, M. Kitano, D. Yamaguchi, H. Kato, S. Hayashi, M. Hara, J. Am. Chem. Soc. 130, 12787–12793 (2008)

    CAS  PubMed  Google Scholar 

  26. S. Suganuma, K. Nakajima, M. Kitano, D. Yamaguchi, H. Kato, S. Hayashi, M. Hara, Solid State Sci. 12, 1029–1034 (2010)

    CAS  Google Scholar 

  27. D. Yamaguchi, M. Hara, Solid State Sci. 12, 1018–1023 (2010)

    CAS  Google Scholar 

  28. K. Nakajima, M. Hara, ACS Catal. 2, 1296–1304 (2012)

    CAS  Google Scholar 

  29. P.A. Russo, M.M. Antunes, P. Neves, P.V. Wiper, E. Fazio, F. Neri, F. Barreca, L. Mafra, M. Pillinger, N. Pinna, A.A. Valente, Green Chem. 16, 4292–4305 (2014)

    Google Scholar 

  30. P. Gupta, S. Paul, Green Chem. 13, 2365–2372 (2011)

    CAS  Google Scholar 

  31. T. Yamazaki, K.Y. Numani, M. Goodman, Biopolymers 31, 1513–1528 (1991)

    CAS  PubMed  Google Scholar 

  32. C.A.G.N. Montalbeti, V. Falque, Tetrahedron 61, 10827–10852 (2005)

    Google Scholar 

  33. J.R. Satam, R.V. Jayaram, Catal. Commun. 9, 2365–2370 (2008)

    CAS  Google Scholar 

  34. F. Tamaddon, F. Aboee, A. Nasiri, Catal. Commun. 16, 194–197 (2011)

    CAS  Google Scholar 

  35. J.W. Bode, Curr. Opin. Drug Discov. Devel. 9, 765–775 (2006)

    CAS  PubMed  Google Scholar 

  36. H.R. Shaterian, M. Ghashang, M. Feyzi, Appl. Catal. A 345, 128–133 (2008)

    CAS  Google Scholar 

  37. T. Dingermann, D. Steinhilber, G. Folkers, Molecular Biology in Medicinal Chemistry, vol. 21 (Wiley-VCH, Weinheim, 2004), pp. 381–398

    Google Scholar 

  38. A.Y. Shen, C.L. Chen, C.I. Lin, Chin. J. Physiol. 35, 45–54 (1992)

    CAS  PubMed  Google Scholar 

  39. F. Al-Assar, K.N. Zelenin, E.E. Lesiovskaya, I.P. Bezhan, B.A. Chakchir, Pharm. Chem. J. 36, 598–603 (2002)

    CAS  Google Scholar 

  40. P.V. Pallai, R.S. Struthers, M. Goodman, L. Moroder, E. Wunsch, W. Vale, Biochemistry 24, 1933–1941 (1985)

    CAS  PubMed  Google Scholar 

  41. M. Sechi, U. Azzena, M.P. Delussu, R. Dallocchio, A. Dessi, A. Cosseddu, N. Pala, N. Neamati, Molecules 13, 2442–2461 (2008)

    CAS  PubMed  PubMed Central  Google Scholar 

  42. C. Aleman, J. Puiggali, J. Org. Chem. 60, 910–924 (1995)

    CAS  Google Scholar 

  43. N.P. Selvam, S. Saranya, P.T. Perumal, Can. J. Chem. 85, 32–38 (2008)

    Google Scholar 

  44. H.R. Sadaati-Mosgtaghin, F.M. Zonoz, M.M. Amini, J. Solid State Chem. 260, 16–22 (2018)

    Google Scholar 

  45. B. Maleki, M. Bhagayeri, RSC Adv. 5, 79746–79758 (2015)

    CAS  Google Scholar 

  46. H.A. Soliman, A.Y. Mubarak, S.S. Elmorsy, Chin. Chem. Lett. 27, 353–356 (2016)

    CAS  Google Scholar 

  47. R.P. Bakhshani, A. Hassanabadi, J. Chem. Res. 40, 35 (2016)

    Google Scholar 

  48. T.L. Lambat, S.S. Deo, F.S. Inam, T.B. Deshmukh, A.R. Bhat, Karbala Int. J. Mod. Sci. 2, 63–68 (2016)

    Google Scholar 

  49. F.M. Moghaddam, G. Tavakoli, B. Saeednia, Chem. Sel. 2, 1316–1322 (2017)

    CAS  Google Scholar 

  50. G. Ramachandran, R. Saraswathi, M. Kumarraja, P. Govindaraj, T. Subramanian, Synth. Commun. 48, 216–222 (2018)

    CAS  Google Scholar 

  51. B. Mohammadi, B.R. Khorrami, Montash. Chem. 149, 1089 (2018)

    CAS  Google Scholar 

  52. J. Ungar, F. Robinson, J. Pharmacol. Exp. Ther. 80, 217–232 (1944)

    CAS  Google Scholar 

  53. I. Antonini, P. Polucci, L.R. Kelland, E. Menta, N. Pescalli, S. Martelli, J. Med. Chem. 42, 2535–2541 (1999)

    CAS  PubMed  Google Scholar 

  54. P.J. McCarthy, T.P. Pitts, G.P. Gunawardana, M. Kelly-Borges, S.A. Pomponi, J. Nat. Prod. 55, 1664–1668 (1992)

    CAS  PubMed  Google Scholar 

  55. D.P. Spalding, E.C. Chapin, H.S. Mosher, J. Org. Chem. 19, 357 (1954)

    CAS  Google Scholar 

  56. N. Filloux, J.P. Galy, Synlett 9, 1137–1139 (2001)

    Google Scholar 

  57. I. Antonini, P. Polucci, A. Magnano, D. Cacciamani, M.T. Konieczny, J. Paradziej-Łukowicz, S. Martelli, Bioorg. Med. Chem. 11, 399–405 (2003)

    CAS  PubMed  Google Scholar 

  58. M.A. Pasha, R.R. Khan, K.B. Ramesh, Can. Chem. Trans. 4, 90–98 (2016)

    CAS  Google Scholar 

  59. S. Rahmani, A. Amoozadeh, J. Nanostruct. 4, 83–93 (2014)

    Google Scholar 

  60. M. Nasr-Esfahani, M. Montazerozohori, T. Abdizadeh, C. R. Chimie 18, 547–553 (2015)

    CAS  Google Scholar 

  61. M. Kiani, M. Mohammadipour, RSC Adv. 7, 997–1007 (2017)

    CAS  Google Scholar 

  62. R. Sarada, V. Jagannadharao, B. Govindh, M. Padma, Int. J. Chemtech. Res. 10, 1011–1117 (2017)

    CAS  Google Scholar 

  63. A. Jain, S. Singh, K.R. Tiwari, N. Kumar, R. Tomar, Int. J. Mater. Sci. 13, 189–204 (2018)

    Google Scholar 

  64. R. Karmakar, A. Bhaumik, B. Banerjee, C. Mukhopadhyay, Tetrahedron Lett. 58, 622–628 (2017)

    CAS  Google Scholar 

  65. H. Sharghi, P. Shiri, M. Aberi, Beilstein J. Org. Chem. 14, 2745–2770 (2018)

    CAS  PubMed  PubMed Central  Google Scholar 

  66. K. Nikoofar, F.M. Yielzoleh, J. Saudi Chem. Soc. 22, 715–741 (2018)

    CAS  Google Scholar 

  67. M. Mokhtary, Acad. J. Polym. Sci. 2, 555580 (2018)

    Google Scholar 

  68. A. Murugesan, R.M. Gengan, K.G. Moodley, G. Gericke, Adv. Mater. Lett. 8, 773–782 (2017)

    CAS  Google Scholar 

  69. H. Singh, H. Singh, A. Singh, M.K. Gupta, S. Sharma, P.M.S. Bedi, Indian J. Pharm. Sci. 79, 801–812 (2017)

    Google Scholar 

  70. S. Mao, F. Li, Y. Lv, C. Lv, S. Yu, Heterocycles 94, 1895–1902 (2017)

    CAS  Google Scholar 

  71. F. Hatamjafari, O.H. Lazarjani, Rev. Roum. Chim. 62, 255–260 (2017)

    Google Scholar 

  72. G.J. Bennett, H.H. Lee, Phytochemistry 28, 967–998 (1989)

    CAS  Google Scholar 

  73. Y. Na, J. Pharm. Pharmacol. 61, 707–712 (2009)

    CAS  PubMed  Google Scholar 

  74. A.N. Dadhania, V.K. Patel, D.K. Raval, J. Saudi Chem. Soc. 21, S163–S169 (2017)

    CAS  Google Scholar 

  75. S. Samantaray, P. Kar, G. Hota, B.G. Mishra, Ind. Eng. Chem. Res. 52, 5862–5870 (2013)

    CAS  Google Scholar 

  76. O. Sirkecioglu, N. Talinli, A. Akar, J. Chem. Res. 86, 502–506 (1995)

    Google Scholar 

  77. A. Banerjee, A.K. Mukherjee, Stain Technol. 56, 83–85 (1981)

    CAS  PubMed  Google Scholar 

  78. J. Liu, Z. Diwu, W.Y. Leung, Bioorg. Med. Chem. Lett. 11, 2903–2905 (2001)

    CAS  PubMed  Google Scholar 

  79. G. Song, B. Wang, H. Luo, L. Yang, Catal. Commun. 8, 673–676 (2007)

    CAS  Google Scholar 

  80. S. Kantevari, R. Bantu, L. Nagarapu, Arkivoc 16, 136–148 (2006)

    Google Scholar 

  81. F. Nemati, S. Sabaqian, J. Saudi Chem. Soc. 21, S383–S393 (2017)

    CAS  Google Scholar 

  82. S. Maripi, R.B. Korupolu, S.B. Madasu, GSC 7, 70–84 (2017)

    CAS  Google Scholar 

  83. A.B. Waghamare, S.S. Deshmukh, G.M. Bondle, A.V. Chate, Chem. Biol. Interact. 8, 151–153 (2018)

    Google Scholar 

  84. S.V. Deshmukh, G.K. Kadam, S.V. Shisodia, M.V. Katarina, S.B. Vbale, R.P. Pawar, Int. J. Phys. Chem. Sci. 7, 75 (2018)

    CAS  Google Scholar 

  85. B.M. Sapkal, A.J. Sahani, A.S. Burange, S. Kale, G. Abraham, S. Disale, Curr. Catal. 7, 144 (2018)

    CAS  Google Scholar 

  86. F.N. Sadeh, M. Fatehpour, N. Hazeri, M.T. Maghsoodlou, M. Lashkari, Acta Chem. Iasi 25, 24 (2017)

    Google Scholar 

  87. S. Karhale, M. Patil, G. Rashinkar, V. Helavi, Res. Chem. Intermed. 43, 7073–7086 (2017)

    CAS  Google Scholar 

  88. M. Pirouzmand, A.M. Gharehbaba, Z. Ghasemi, S.A. Khaaje, Arab. J. Chem. 10, 1070 (2017)

    CAS  Google Scholar 

  89. R.R. Magar, G.T. Pawar, S.P. Gadekar, M.K. Lande, Bull. Chem. React. Eng. Catal. 13, 436–446 (2018)

    Google Scholar 

  90. M.B. Swami, A.H. Jadhav, N.V. Ghule, S.S. Mahurkar, S.R. Mathapati, A.N. Patil, S.G. Patil, IJGHC 7, 788 (2018)

    CAS  Google Scholar 

  91. B. Karami, K. Eskandari, G. Ansari, Der. Chemica. Sinica. 8, 342 (2017)

    CAS  Google Scholar 

  92. S.B. Pore, Asian J. Chem. 30, 2621–2624 (2018)

    CAS  Google Scholar 

  93. S.U. Deshmukh, G.K. Kadam, S.U. Shisodia, M.V. Katarina, S.B. Ubale, R.P. Pawar, IJCPS 7, 1 (2018)

    Google Scholar 

  94. S.M. Vahdat, M. Akbari, Orient. J. Chem. 24, 1573–1580 (2011)

    Google Scholar 

  95. B. Aday, Y. Yildiz, R. Ulus, S. Eris, F. Sen, M. Kaya, New J. Chem. 40, 748–754 (2016)

    CAS  Google Scholar 

  96. Y.B. Shen, G.W. Wang, Arkivoc 16, 1–8 (2008)

    Google Scholar 

  97. B. Das, P. Thirupathi, I. Mahender, V.S. Reddy, Y.K. Rao, J. Mol. Catal. A Chem. 247, 233–239 (2006)

    CAS  Google Scholar 

  98. S. Kumari, A. Shekhar, D. Pathak, Chem. Sci. Trans. 3, 652–663 (2014)

    Google Scholar 

  99. G.M. Sheldrick, Acta Cryst. A 64, 112–122 (2008)

    CAS  Google Scholar 

  100. G. Ramachandran, R. Saraswathi, M. Kumarraja, P. Govindaraj, T. Subramanian, Synth. Commun. 48, 216–222 (2018)

    CAS  Google Scholar 

  101. N. Azizi, M. Alipour, J. Mol. Liq. 206, 268–271 (2015)

    CAS  Google Scholar 

  102. H.A. Soliman, A.Y. Mubarak, S.S. Elmorsy, Chin. Chem. Lett. 27, 353–356 (2016)

    CAS  Google Scholar 

  103. S. Khabnadideh, K. Zomorodian, B.B.F. Mirjalili, E. Izadi, L. Zamani, J. Chil. Chem. Soc. 61, 3116 (2016)

    Google Scholar 

  104. K. Selvakumar, T. Shanmugaprabha, M. Kumaresan, P. Sami, Synth. Commun. 47, 2115–2126 (2017)

    CAS  Google Scholar 

  105. A. Khojastehnezhad, F. Moeinpour, M. Vafaei, J. Mex. Chem. Soc. 59, 29–35 (2015)

    CAS  Google Scholar 

  106. A.P. Marjani, J. Khalafy, S. Mahmoodi, ARKIVOC iii, 262–270 (2016)

    Google Scholar 

  107. S.-J. Yü, S. Wu, X.-M. Zhao, C.-W. Lü, Res. Chem. Intermed. 43, 3121–3130 (2017)

    Google Scholar 

  108. G.D. Shirole, S. Bhalekar, S.N. Shelke, Indian J. Chem. 57B, 1430–1435 (2018)

    CAS  Google Scholar 

  109. M.A. Mangalavathi, J. Pasha, Chem. Chem. Sci. 8, 1009–1017 (2018)

    Google Scholar 

  110. M. Pirouzmand, A.M. Gharehbaba, Z. Ghasemi, S.A. Khaaje, Arab. J. Chem. 10, 1070–1076 (2017)

    CAS  Google Scholar 

  111. F. Nemati, S. Sabaqian, J. Saudi Chem. Soc. 21, S383–S393 (2017)

    CAS  Google Scholar 

  112. S. Maripi, R.B. Korupolu, S.B. Madasu, Green Sustain. Chem. 7, 70–84 (2017)

    CAS  Google Scholar 

  113. A. Thakur, A. Sharma, A. Sharma, Synth. Commun. 46, 1766–1771 (2016)

    CAS  Google Scholar 

  114. R. Khoeiniha, A. Ezabadia, A. Olyaei, Iran. Chem. Commun. 4, 273–282 (2016)

    CAS  Google Scholar 

  115. K. Hemalatha, G. Madhumitha, A. Kajbafvala, N. Anupama, R. Sompalle, S.M. Roopan, J. Nanomater. 2013, 1–23 (2013)

    Google Scholar 

  116. S. Erdem, B. Erdem, R.M. Oksuzoglu, Open Chem. 16, 923–929 (2018)

    CAS  Google Scholar 

  117. F.D. Guerra, M.F. Attia, D.C. Whitehead, F. Alexis, Molecules 23, 1760 (2018)

    PubMed Central  Google Scholar 

  118. P. Singh, M. Abdullah, S. Ikram, Nano Res. Appl. 2, 1–10 (2016)

    Google Scholar 

  119. M.M. Khin, A.S. Nair, V.J. Babu, R. Murugana, S. Ramakrishna, Energy Environ. Sci. 5, 8075–8109 (2012)

    CAS  Google Scholar 

Download references

Acknowledgements

I am grateful to Director, SAIF, IIT Bombay for SEM, TEM. I also extend my thanks to Prof. R. K. Bamezai, Department of Chemistry, University of Jammu for recording TGA. I am thankful to Prof. H. N. Sheikh for providing me the FTIR analysis. We are also thankful to the department of Physics for providing us the XRD data of the crystal and Dr. Amit Kumar Sharma for providing me the NMR data of the prepared compounds.

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Jammu, Jammu, 180 006, India

    Jaspreet Kour, Monika Gupta & Bushra Chowhan

  2. Department of Physics, University of Jammu, Jammu, 180 006, India

    Vivek K. Gupta

Authors
  1. Jaspreet Kour
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Monika Gupta
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Bushra Chowhan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Vivek K. Gupta
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Monika Gupta.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 82909 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kour, J., Gupta, M., Chowhan, B. et al. Carbon-based nanocatalyst: An efficient and recyclable heterogeneous catalyst for one-pot synthesis of gem-bisamides, hexahydroacridine-1,8-diones and 1,8-dioxo-octahydroxanthenes. J IRAN CHEM SOC 16, 2587–2612 (2019). https://doi.org/10.1007/s13738-019-01723-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-019-01723-1

Keywords

Search

Navigation