Amino acid-incorporated polymer network by thiol-ene polymerization

Abstract

Abstract. Triallyl L-alanine (A3A) and triallyl L-phenylalanine (A3F) were synthesized by reactions of L-alanine and L-phenylalanine with allyl bromide in the presence of sodium hydroxide, respectively. Thiol-ene thermal polymerization of A3A or A3F with pentaerythritol-based primary tetrathiol (pS4P) or pentaerythritol-based secondary tetrathiol (S4P) at allyl/SH 1/1 in the presence of 2,2"-azobis(isobutyronitrile) produced an amino acid-incorporated polymer network (A3A-pS4P, A3A-S4P or A3F-S4P). Although the thermally cured resins were homogeneous and flat films, the corresponding thiol-ene photopolymerization did not give a successful result. Degree of swelling for each thermally cured film in N,Ndimethylformamide was much higher than that in water. The glass transition and 5% weight loss temperatures (T g and T 5 ) of A3F-pS4P and A3F-S4P were higher than those of A3A-pS4P and A3A-S4P, respectively. Also, A3F-pS4P and A3F-S4P exhibited much higher tensile strengths and moduli than A3A-pS4P and A3A-S4P did, respectively. Consequently, A3F-pS4P displayed the highest T g (38.7°C), T 5 (282.0°C), tensile strength (9.5 MPa) and modulus (406 MPa) among all the thermally cured resins.

Synthesis and Characterization of Phenylalanine Nanotubes as Green pH‐Responsive Drug Nanocarriers

“…According to the literatures, there are no significant differences in the FTIR spectra of pure phenylalanine amino acid and their nanotubes. However, in nanotubes due to the movements of PhNT′s aggregation, the intensity of some vibrations is lower than that of pure phenylalanine amino acid [50] …”

The Use of Click-Type Reactions in the Preparation of Thermosets

“…The thiol-ene reaction has been applied with terpenes as starting resins for 3D printing technologies [104] and, in general, to the preparation of thermosetting materials from renewable materials such as lignin [105,106], eugenol [107,108], furan derivatives [109], allylated aminoacids [110] and resveratrol [111]. Keratin, which is a natural polymer found in hair and nails, contains thiols in its cysteine and methionine structures; as such, it has been used as a renewable natural reinforcing agent for photocured thiol-ene coatings [112].…”