Journal
LANGMUIR
Volume 32, Issue 18, Pages 4586-4594Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.langmuir.6b01059
Keywords
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Funding
- National Natural Science Foundation of China [21174018]
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Four cyclo(L-Lys-L-Glu) derivatives (3-6) were synthesized from the coupling reaction of protecting L-lysine with L-glutamic acid followed by the cyclization, deprotection, and protection reactions. They can efficiently gelate a wide variety of organic solvents or water. Interestingly, a spontaneous chemical reaction proceeded in the organogel obtained from 3 in acetone exhibiting not only visual color alteration but also increasing mechanical strength with the progress of time due to the formation of Schiff base. Moreover, 6 bearing a carboxylic acid and Fmoc group displayed a robust hydrogelation capability in PBS solution. Transmission electron microscopy (TEM) and scanning electron microscopy (SEM) revealed the characteristic gelation morphologies of 3D fibrous network structures in the resulting organo- and hydrogels. FT-IR and fluorescence analyses indicated that the hydrogen bonding and pi-pi stacking play as major driving forces for the self-assembly of these cyclic dipeptides as low molecular-weight gelators. X-ray diffraction (XRD) measurements and computer modeling provided information on the molecular packing model in the hydrogelation state of 6. A spontaneous chemical reaction proceeded in the organogel obtained from 3 in acetone exhibiting visual color alteration and increasing mechanical strength. 6 bearing an optimized balance of hydrophilicity to lipophilicity gave rise to a hydrogel in PBS with MGC at 1 mg/mL.
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