Synthesis of Cyclo(L-Lys-L-Lys)-Based Organogelators and Their Applications for Phase-Selective Gelation and Dye Adsorption

doi:10.11944/j.issn.1000-0518.2015.08.140423

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (8): 900-908.DOI: 10.11944/j.issn.1000-0518.2015.08.140423

• Full Papers • Previous Articles Next Articles

Synthesis of Cyclo(L-Lys-L-Lys)-Based Organogelators and Their Applications for Phase-Selective Gelation and Dye Adsorption

GENG Huimin,ZONG Qianying,YOU Jie,YE Lin,ZHANG Aiying,FENG Zengguo()

School of Materials, Beijing Institute of Technology, Beijing 100081, China

Received:2014-12-12 Accepted:2015-05-05 Published:2015-08-08 Online:2015-08-08
Contact: FENG Zengguo
Supported by:
Supported by the National Natural Science Foundation of China(No.21174018)

Abstract

Abstract:

One linear and one macrocyclic tetrapepitides(4 and 5) with Fmoc were synthesized by two ways of Trt protection group cleavage in the preparation of symmetrical tetrapepitides using cysteine-modified cyclo(L-Lys-L-Lys) diketopi-perazines. Both tetrapepitides show excellent capability to gelate a number of organic solvents to give thermo-reversible organogels. The self-assembled fibrillar networks in the organogels were distinctly observed by SEM. Interestingly, two organogelators could selectively gelate common chlorinated organic solvents from their mixture with water, even at a concentration as low as 0.1%(volume fraction). Moreover, the xerogel obtained from the organogel of compound 4 in chloroform can high efficiently adsorb various tested dyes from aqueous solutions due to the larger specific surface area of 3D xerogel network showing a micro- and nano-sized structure and the π-π interaction between dye molecules and Fmoc protection groups. The absorption capacity of the xerogel for those dyes increases with the temperature.

Key words: cyclic dipeptide, organogel, phase-selective gelation, dye adsorption

CLC Number:

GENG Huimin, ZONG Qianying, YOU Jie, YE Lin, ZHANG Aiying, FENG Zengguo. Synthesis of Cyclo(L-Lys-L-Lys)-Based Organogelators and Their Applications for Phase-Selective Gelation and Dye Adsorption[J]. Chinese Journal of Applied Chemistry, 2015, 32(8): 900-908.

References

[1]	Yu X, Chen L, Zhang M, et al.Low-Molecular-Mass Gels Responding to Ultrasound and Mechanical Stress: Towards Self-Healing Materials[J]. Chem Soc Rev, 2014, 43(15): 3-28.
[2]	Smith A M, Williams R J, Tang C, et al.Fmoc-Diphenylalanine Self Assembles to a Hydrogel via a Novel Architecture Based on π-π Interlocked β-Sheets[J]. Adv Mater, 2008, 20(1): 37-41.
[3]	Tang C, Smith A M, Collins R F, et al.Fmoc-Diphenylalanine Self-Assembly Mechanism Induces Apparent pKa Shifts[J]. Langmuir, 2009, 25(16): 9447-9453.
[4]	XIE Zhiguo, ZHANG Aiying, YE Lin, et al.Synthesis and Gelation of a Series of Low-Molecular-Weight Gelators Based on Fmoc-Dipeptide in Alcoholic Solvents[J]. Acta Chim Sin, 2008, 66(23): 2620-2624(in Chinese). 谢志国, 张爱英, 叶霖, 等. 一类Fmoc保护二肽醇类凝胶因子的合成与凝胶化研究[J]. 化学学报, 2008, 66(23): 2620-2624.
[5]	Kar T, Debnath S, Das D, et al.Organogelation and Hydrogelation of Low-Molecular-Weight Amphiphilic Dipeptides: pH Responsiveness in Phase-Selective Gelation and Dye Removal[J]. Langmuir, 2009, 25(15): 8639-8648.
[6]	Sadownik J W, Ulijn R V. Locking an Oxidation-Sensitive Dynamic Peptide System in the Gel State[J]. Chem Commun, 2010, 46(20): 3481-3483.
[7]	Fleming S, Ulijn R V. Design of Nanostructures Based on Aromatic[J]. Chem Soc Rev, 2014, 43(23): 8150-8177.
[8]	Fichman G, Adler-Abramovich L, Manohar S, et al.Seamless Metallic Coating and Surface Adhesion of Self-Assembled Bioinspired Nanostructures Based on Di-(3, 4-dihydroxy-l-phenylalanine) Peptide[J]. ACS Nano, 2014, 8(7): 7220-7228.
[9]	Xie Z G, Zhang A Y, Ye L, et al.Organo- and Hydrogels Derived from Cyclo(L-Tyr-L-Lys) and Its ε-Amino Derivatives[J]. Soft Matter, 2009, 5(7): 1474-1482.
[10]	Yan X, Zhu P, Li J. Self-Assembly and Application of Diphenylalanine-Based Nanostructures[J]. Chem Soc Rev, 2010, 39(6): 1877-1890.
[11]	Aggeli A, Bell M, Boden N, et al.Engineering of Peptide b-Sheet Nanotapes[J]. J Mater Chem, 1997, 7(7): 1135-1145.
[12]	Peng J, Xia H, Liu K, et al.Water-in-Oil Gel Emulsions from a Cholesterol Derivative: Structure and Unusual Properties[J]. J Colloid Interface Sci, 2009, 336(2): 780-785.
[13]	HOU Xiaoyu, LIU Kaiqiang, FANG Yu. Progress in the Studies of Low Molecular Mass Gelators with Phase-Selective Gelation Properties[J]. Chinese J Appl Chem, 2011, 28(11): 1221-1230(in Chinese). 侯晓育, 刘凯强, 房喻. 具有选择性凝胶能力的小分子凝胶剂研究进展[J]. 应用化学, 2011, 28(11): 1221-1230.
[14]	Bhattacharya S, Krishnan-Ghosh Y. First Report of Phase Selective Gelation of Oil from Oil/Water Mixtures. Possible Implications Toward Containing Oil Spills[J]. Chem Commun, 2001: 185-186.
[15]	Jadhav S R, Vemula P K, Kumar R, et al.Sugar-Derived Phase-Selective Molecular Gelators as Model Solidifiers for Oil Spills[J]. Angew Chem Int Ed, 2010, 49(42): 7695-7698.
[16]	Basak S, Nanda J, Banerjee A. A New Aromatic Amino Acid Based Organogel for Oil Spill Recovery[J]. J Mater Chem, 2012, 22(23): 11658-11664.
[17]	HUANG Yisui, YNG Fafu, GUO Hongyu. Synthesis and Properties of Cellulose Resin Crosslinked with Perylene Tetracarboxylic Diimides[J]. Chinese J Appl Chem, 2014, 31(8): 892-900(in Chinese). 黄一绥, 杨发福, 郭红玉. 苝酰亚胺接枝纤维素的合成与染料吸附性能[J]. 应用化学, 2014, 31(8): 892-900.
[18]	Tang Y T, Dou X Q, Ji Z A, et al.C2-Symmetric Cyclohexane-based Hydrogels: A Rational Designed LMWG and Its Application in Dye Scavenging[J]. J Mol Liq, 2013, 177: 167-171.
[19]	Kaur N, Zhou B, Breitbeil F, et al.A Delineation of Diketopiperazine Self-Assembly Processes Understanding the Molecular Events Involved in N-(Fumaroyl)diketopiperazine of L-Lys(FDKP) Interactions[J]. Mol Pharm, 2007, 5(2): 294-315.
[20]	Majó M A, Bou J J, Herranz C, et al.Polycondensation of L-Lysine Diketopiperazine with Tartaric Acid-Evidence on the Formation of Cyclic Oligomers[J]. Macromol Chem Phys, 2006, 207(6): 615-620.
[21]	Dou X, Li P, Zhang D, Feng C L. C2-Symmetric Benzene-based Hydrogels with Unique Layered Structures for Controllable Organic Dye Adsorption[J]. Soft Matter, 2012, 8(11): 3231-3238.

Synthesis of Cyclo(L-Lys-L-Lys)-Based Organogelators and Their Applications for Phase-Selective Gelation and Dye Adsorption

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 2

Recommended Articles

Metrics

Comments

[1]	HOU Xiaoyu, LIU Kaiqang, FANG Yu*. Progress in the Studies of Low-Molecular Mass Gelators with Phase-Selective Gelation Properties [J]. Chinese Journal of Applied Chemistry, 2011, 28(11): 1221-1228.
[2]	Tong Yuejin, Ding Mengxian. ASYMMETRIC SYNTHESIS OF AROMATIC CYANOHYDRINS CATALYSED BY CYCLO(L-Phe-L-His) [J]. Chinese Journal of Applied Chemistry, 1990, 0(1): 23-27.