@article{FolikumahNeffeBehletal.2019,
  author    = {Folikumah, Makafui Yao and Neffe, Axel T. and Behl, Marc and Lendlein, Andreas},
  title     = {Thiol Michael-Type reactions of optically active mercapto-acids in aqueous medium},
  series = {MRS advances : a journal of the Materials Research Society},
  volume    = {4},
  journal   = {MRS advances : a journal of the Materials Research Society},
  number    = {46-47},
  publisher = {Springer Nature Switzerland AG},
  address   = {Cham},
  issn      = {2059-8521},
  doi       = {10.1557/adv.2019.308},
  pages     = {2515 -- 2525},
  year      = {2019},
  abstract  = {Defined chemical reactions in a physiological environment are a prerequisite for the in situ synthesis of implant materials potentially serving as matrix for drug delivery systems, tissue fillers or surgical glues. 'Click' reactions like thiol Michael-type reactions have been successfully employed as bioorthogonal reaction. However, due to the individual stereo-electronic and physical properties of specific substrates, an exact understanding their chemical reactivity is required if they are to be used for in-situ biomaterial synthesis. The chiral (S)-2-mercapto-carboxylic acid analogues of L-phenylalanine (SH-Phe) and L-leucine (SH-Leu) which are subunits of certain collagenase sensitive synthetic peptides, were explored for their potential for in-situ biomaterial formation via the thiol Michael-type reaction. In model reactions were investigated the kinetics, the specificity and influence of stereochemistry of this reaction. We could show that only reactions involving SH-Leu yielded the expected thiol-Michael product. The inability of SH-Phe to react was attributed to the steric hindrance of the bulky phenyl group. In aqueous media, successful reaction using SH-Leu is thought to proceed via the sodium salt formed in-situ by the addition of NaOH solution, which was intented to aid the solubility of the mercapto-acid in water. Fast reaction rates and complete acrylate/maleimide conversion were only realized at pH 7.2 or higher suggesting the possible use of SH-Leu under physiological conditions for thiol Michael-type reactions. This method of in-situ formed alkali salts could be used as a fast approach to screen mercapto-acids for thio Michael-type reactions without the synthesis of their corresponding esters.},
  language  = {en}
}
@article{FriessWischkeLendlein2019,
  author    = {Friess, Fabian and Wischke, Christian and Lendlein, Andreas},
  title     = {Microscopic analysis of shape-shiftable oligo(epsilon-caprolactone)-based particles},
  series = {MRS advances},
  volume    = {4},
  journal   = {MRS advances},
  number    = {59-60},
  publisher = {Cambridge Univ. Press},
  address   = {New York},
  issn      = {2059-8521},
  doi       = {10.1557/adv.2019.392},
  pages     = {3199 -- 3206},
  year      = {2019},
  abstract  = {Spherical particles are routinely monitored and described by hydrodynamic diameters determined, e.g., by light scattering techniques. Non-spherical particles such as prolate ellipsoids require alternative techniques to characterize particle size as well as particle shape. In this study, oligo(epsilon-caprolactone) (oCL) based micronetwork (MN) particles with a shape-shifting function based on their shape-memory capability were programmed from spherical to prolate ellipsoidal shape aided by incorporation and stretching in a water-soluble phantom matrix. By applying light microscopy with automated contour detection and aspect ratio analysis, differences in characteristic aspect ratio distributions of non-crosslinked microparticles (MPs) and crosslinked MNs were detected when the degrees of phantom elongation (30-290\%) are increased. The thermally induced shape recovery of programmed MNs starts in the body rather than from the tips of ellipsoids, which may be explained based on local differences in micronetwork deformation. By this approach, fascinating intermediate particle shapes with round bodies and two opposite sharp tips can be obtained, which could be of interest, e.g., in valves or other technical devices, in which the tips allow to temporarily encage the switchable particle in the desired position.},
  language  = {en}
}