Synthesis, characterization, and application of monodisperse poly L-Dopa microspheres
In this study, 3,4-dihydroxy-L-phenylalanine (L-Dopa) was solvothermally polymerized to monodisperse microspheres 1 μμm in diameter. Polymerization was carried out in dimethylformamide containing appropriate amounts of urea and L-Dopa at 120 ∘∘C for 24 h. Synthesis of the polymer in basic aqueous solution under hydrothermal conditions or via conventional heating resulted in the formation of bulky powders including irregularly shaped particles of the polymer. The morphologies of the synthesized polymers were characterized by scanning electron microscopy (SEM). The microspheres synthesized by solvothermal method (with ∼∼1 μμm average diameter) were clearly observable in SEM micrographs. The thermal stability of the synthesized polymer was studied by thermogravimetry and differential scanning calorimetry techniques. It was recognized that the polymer is thermally stable at more than 200 ∘∘C. Applicability of the polymer microspheres was investigated for catalyzing the reaction of one-pot multicomponent synthesis of dihydrofurans. Several dihydrofuran derivatives were successfully synthesized using poly L-Dopa as a novel, environmentally friendly, and efficient catalyst with efficiency of more than 90%. Poly L-Dopa is easily separated by filtration from the reaction mixture. It can be used several times without decreasing the catalyzing activity after washing by suitable solvents.
___
- Mozaffari, S; Nateghi, M. R.; Borhani Zarandi, M.
Sol. Energy
2014
,
106
, 63-71.
- Ryou, M. H.; Kim, J.; Lee, I.; Kim, S.; Jeong, Y. K.; Hong, S.; Ryu, J. H.; Kim, T. S.; Park, J. K.; Lee, H. et al.
Adv. Mater.
2013
,
25
, 1571-1576.
- Kong, J.; Yee, W. A.; Yang, L.; Wei, Y.; Phua, S. L.; Ong, H. G.; Ang, G. M.; Li, X.; Lu, X.
Chem. Commun.
2012
,
48
, 10316-10318.
- Goodenough, J. B.; Park, K. S.
J. Am. Chem. Soc.
2013
,
135
, 1167-1176.
- Lynge, M. E.; van der Westen, R.; Postma, A.; Stadler, B.
Nanoscale
2011
,
3
, 4916-4928.
- Low, W. C.; Rujitanaroj, P. O.; Lee, D. K.; Messersmith, P. B.; Stanton, L. W.; Goh, E.; Chew, S. W.
Biomaterials
2013
,
34
, 3581-3590.
- Wang, K.; Luo, Y.
Biomacromolecules
2013
,
14
, 2373-2382.
- Li, W.; Wang, J. S.; Ren, J. S.; Qu, X. G.
Angew. Chem. Int. Ed.
2013
,
52
, 6726-6730.
- Gao, H. C.; Sun, Y. M.; Zhou, J. J.; Xu, R.; Duan, H. W.
ACS Appl. Mater. Interfaces
2013
,
5
, 425-432.
- Fu, Y. C.; Li, P. H.; Xie, Q. J.; Xu, X. H.; Lei, L. H.; Chen, C.; Zou, C.; Deng, W. F.; Yao, S. Z.
Adv. Funct.
Mater.
2009
,
19
, 1784-1791.
- Li, F.; Feng, Y.; Yang, L.; Li, L.; Tang, C.; Tang, B. A.
Biosens. Bioelectron
.
2011
,
26
, 2489-2494.
- Yu, Y. M.; Zhang, J. H.; Xiao, C. H.; Zhong, J. D.; Zhang, X. H.; Chen, J. H.
Fuel Cells
2012
,
12
, 506-510.
- Liu, Y.; Ai, K.; Lu, L.
Chem. Rev
.
2014
,
114
, 5057-5115.
- Xiong, S.; Wang, Y.; Zhu, J.; Yu, J.; Hu, Z.
Langmuir
2015,
13
, 5504-5512.
- Liu, S.; Fu, J.; Wang, M.; Yan, Y.; Xin, Q.; Cai, L.; Xu, Q. J.
Colloid Interface Sci
.
2016
,
469
, 69-77.
- Liu, Y.; Li, X.; Qin, Y.; Guo, R.; Zhang, J. J.
Appl. Polymer Sci.
2017
,
134
, 44564.
- Zheng, W.; Fan, H.; Wang, L.; Jin, Z.
Langmuir
2015
,
31
, 11671-11677.
- Chen, T.; Liu, T.; Su, T.; Liang, J.
Langmuir
2017
,
33
, 5863-5871.
- Azari, S.; Zou, L.
J. Mem. Sci.
2012
,
401-402
, 68-75.
- Yu, L.; Liu, X.; Yuan, W.; Brown, L. J.; Wang, D.
Langmuir
2015
,
31
, 6351-6366.
- Siddiqui, I. R.; Shamim, S.; Rai, P.; Waseem, M. A.; Abumhdi, A. A.
Tetrahedron Lett
.
2013
,
54
, 6991-6994.
- Shi, R. G.; Wang, X. H.; Liu, R.; Yan, C. G.
Chem. Commun
.
2016
,
52
, 6280-6283.
- Yavari, I.; Hossaini, Z.; Khalilzadeh, M. A.
J. Org. Chem
.
2009
,
2
, 100-102.
- Jadhav, S. A.; Omprakash, S.
Elixir Org. Chem
.
2016
,
90
, 37490-37495.
- Thi, T. A. D.; Depetter, Y.; Mollet, K.; Phuong, H. T.; Ngoc, D. V.; The, C. P.; Van Nguyen, T.
Tetrahedron Lett
.
2015
,
56
, 2422-2425.
- Vinosha, B.; Perumal, S.; Renuga, S.; Almansour, A. I.
Tetrahedron Lett
.
2012
,
53
, 962-966.
- Golchin, S.; Mosslemin, M. H.; Yazdani-Elah-Abadi, A.; Shams, N.
Res. Chem. Intermed.
2017,
43
, 1735-1749.
- Ceylan, M.; Fındık E.
Synth. Commun
.,
2009
,
39
, 1046-1054.
- Wu, T. S.; Li, C. Y.; Leu, Y. L.; Hu, C. Q.
Phytochemistry
1999
,
50
, 509-512.
- Lee, J.; Li, J. H.; Oya, S.; Snyder, J. K. J.
J. Org. Chem.
1992
,
57
, 5301-5312.
- Lipshutz, B. H.
Chem. Rev
.
1986,
86
, 795-819.
- Wang, Q.; Hou, H.; Hui, L.; Yan, C.
J. Org. Chem
.
2009
,
74
, 7403-7406.
- Altieri, E.; Cordaro, M.; Grassi, G.; Risitano, F.; Scala, A.
Tetrahedron
2010
,
66
, 9493-9496.
- Khan, A.; Lal, M.; Sidick Basha, R.
Synthesis
2013
,
45
, 406-412.
- Kumar, R.; Wadhwa, D.; Hussain, K.; Prakash, G.
Syn. Commun
.
2013
,
43
, 1802-1807.
- Karanjule, N. B.; Samant, S. D.
Current Microwave Chem
.
2014
,
1
, 135-141.
- Dutta, L.; Sharma, M.; Bhuyan, P. J.
Tetrahedron
2016
,
72
, 6654-6660.
- An, L.; Sun, X.; Zhang, L.; Zhou, J.; Zhu, F.; Shen, Z.
Chem. Res
.
2016
,
40
, 698-703.
- Tangeti, V. S.; Siva Prasad, G. V.; Panda, J.; Varma, K. R.
Synth. Commun
.
2016
,
46
, 878-884.
- Saralidze, K.; Koole, L. H.; Knetsch, M. L. W.
Materials
2010
,
3
, 3537-3564.