A new platform for the post-functionalization of porous polymer under thermal solvent-free conditions; as a highly efficient and recyclable PTC containing nanocavity
محورهای موضوعی : Materials Synthesis and processing
سمیه الهی
1
,
mehrdad khodadoost
2
,
elham shahidizadeh
3
1 - گروه مهندسی شیمی، واحد آبادان، دانشگاه آزاد اسلامی ، آبادان، ایران
2 - Research Center for Environmental Contaminats (RCEC), Abadan University of Medical Sciences, Abadan, Iran
3 - Research Center for Environmental Contaminats (RCEC), Abadan University of Medical Sciences, Abadan, Iran
کلید واژه: Thermal solvent- free conditions, one-pot reaction, polymer supported ionic liquid, phase transfer catalyst, heterogeneous catalyst, porous polymer, azidohydrins.,
چکیده مقاله :
In this work, for the first time, functionalized 3D-network polymer was synthesized through thermal solvent-free method. The synthetic steps include (1) the preparation of ionic liquid (1-methyl-3-(trimethoxysilylpropyl) imidazolium choloride) [pmim]Cl, (2) synthesis of the 3D-network polymer based on calix[4]resorcinarene, and finally (3) immobilization of ionic liquid on the synthesize polymer through one-pot solvent-free conditions.
The formation of this cationic porous polymer was confirmed by elemental analysis, scanning electron microscopy (SEM), thermal gravimetric analysis (TGA) and derivative thermogravimetric (DTG). Taken together, the results reveal the successful preparation of the efficient and wondrous mesoporous cationic polymer with the simultaneously merged properties of ionic liquid and polymeric matrix on the basis of calix[4]resorcinarene.
One-pot conditions, thermal solvent-free pathway, easy reaction handling and work up, green and affordable methodology, gaining high yields of product are the most important advantages of the present method for the synthesis of this polymeric heterogeneous catalyst.
The hydrophobic central cavity and hydrophilic cationic arms render it a suitable heterogeneous phase transfer catalyst for the preparation of azidohydrins in water. The recovered catalyst could be used for several times without any significant loss of activity.
In this work, for the first time, functionalized 3D-network polymer was synthesized through thermal solvent-free method. The synthetic steps include (1) the preparation of ionic liquid (1-methyl-3-(trimethoxysilylpropyl) imidazolium choloride) [pmim]Cl, (2) synthesis of the 3D-network polymer based on calix[4]resorcinarene, and finally (3) immobilization of ionic liquid on the synthesize polymer through one-pot solvent-free conditions.
The formation of this cationic porous polymer was confirmed by elemental analysis, scanning electron microscopy (SEM), thermal gravimetric analysis (TGA) and derivative thermogravimetric (DTG). Taken together, the results reveal the successful preparation of the efficient and wondrous mesoporous cationic polymer with the simultaneously merged properties of ionic liquid and polymeric matrix on the basis of calix[4]resorcinarene.
One-pot conditions, thermal solvent-free pathway, easy reaction handling and work up, green and affordable methodology, gaining high yields of product are the most important advantages of the present method for the synthesis of this polymeric heterogeneous catalyst.
The hydrophobic central cavity and hydrophilic cationic arms render it a suitable heterogeneous phase transfer catalyst for the preparation of azidohydrins in water. The recovered catalyst could be used for several times without any significant loss of activity.
[1] Dyke CA, Tour JM (2003) J Am Chem Soc 125:1157
[2] Phonthamachai N, Chia H, Li X, Wang F, Tjiu WW, He C (2010) Polymer 5:5377
[3] Molaei S, Ghadermazi M, Molaei N (2022) Rec Chem Intermed 48:771
[4] Zhao W, Ding Y, Zhang Z, Ma B, Qiu W (2011) Reac Kinet Mech and Cat 102:93
[5] Vivekanand PA, Wang ML, Hsieh YM (2013) Molecules 18:2419
[6] Arora KD, Singh S (2006) Tetrahedron Lett 47:4205
[7] Shaterian HR, Ghashang M, Feyzi M (2008) Appl Catal A 345:128
[8] Knops-Gerrits PP, Devos DE, Thibaultstarzyk F, Jacobs PA (1994) Nature 369:543
[9] Chen AJ, Wong ST, Hwang CC, Mou CY (2011) ACS Catal 1:786
[10] Wang L, Meng XJ, Wang B, Chi WY, Xiao FS (2010) Chem Commun 46:5003
[11] Sahoo S, Lundberg H, Eden M, Ahlsten N, Wan W, Zou XD, Martin-Matute B (2012) Chem Cat Chem 4:243
[12] Liang XH, George SM, Weimer AW (2007) Chem Mater 19:5388
[13] Li J, Zhang Y (2007) Chem Mater 19: 2581
[14] Zhang Y, Wang JN, He Y, He YY, Xu BB, Wei S, Xiao FS (2011) Langmuir 27:12585
[15] Mouradzadegun A, Elahi S, Ghanbarzadeh P, (2015) Phosphorus Sulfur Silicon Relat Elem 11:2031
[16] Davarpanah J, Rezaee P, Elahi S (2015) Res Chem Intermed 41:9903
[17] Mouradzadegun A, Najafi Z, Elahi S (2015) J Sulphur Chem 36:624
[18] Mouradzadegun A, Abadast F, Elahi S, Askarikia N (2016) Res Chem Intermed 42: 3147
[19] Mouradzadegun A, Elahi S, Abadast F (2016) Res Chem Intermed 42:1583
[20] Davarpanah J, Elahi S, Rezaee P, (2017) J Porous Mater 25:1
[21] Mouradzadegun A, Elahi S, Abadast F (2014) RSC Advances 4:31239
[22] Mouradzadegun A, Abadast F, Elahi S (2014) Monatsh Chem 145:1663
[23] Mouradzadegun A, Elahi S, Abadast F (2014) Synthesis 47:630
[24] Tunstad LM, Tucker JA, Dalcanale E, Weiser J, Bryant JA, Sherman JC, Helgeson RC, Knobler CB, Cram DJ (1989) J Org Chem 54:1305
[25] Awad WH, Gilman JW, Nydena M, Harris RH, Sutto Jr T E, Callahan J, Trulove PC, DeLong HC, Fox DM (2004) Thermochim Acta 409:3
[26] Mouradzadegun A, Kiasat AR, Kazemian Fard P (2012) Catal Commun 29:1
[27] Davarpanah J, Kiasat AR (2013) RSC Adv 4:4403
[28] Budhathoki-Uprety J, Novak BM (2010) Polymer 51:2140
[29] Kiasat AR, Mouradzadegun A, Saghanezhad SJ (2013) Chin J Catal 34:1861
[30] Gupta P, Paul S (2011) Green Chem 13:2365
[31] Hajjamia M, Ghorbanib F, Bakhtia F (2014) Appl Catal 470:303
[32]. Coe DM, Myers PL, Parry DM, Roberts SM, Storer RJ (1990) J Chem Soc Chem Commun 2:151
[33] Chen SW, Thakur SS, Li W, Shin CK, Kawthekar RB, Kim GJ (2006) J Mol Catal 259: 116
[34] Kiasat AR, Badri R, Zargar B, Sayyahi S (2008) J Org Chem 73:8382
[35 Mouradzadegun A, Elahi S, Abadast F (2014) Catal Lett 144:1636
[36] Kiasat AR, Zayadi M, (2008) Catal Commun 9:2063
[37] Tamami B, Mahdavi H (2001) Tetrahedron Lett 42:8721
