Property tuning by fluorination is very effective for a number of purposes, and currently increasingly investigated for aliphatic compounds. An important application is lipophilicity (log P) modulation. However, the determination of log P is cumbersome for non-UV-active compounds. A new variation of the shake-flask log P determination method is presented, enabling the measurement of log P for f...

Solventless mechanochemical synthesis represents a technique with improved sustainability metrics compared to solvent-based processes. Herein, we describe a methodical process to run one solventless reaction directly into another through multistep mechanochemistry, effectively amplifying the solvent savings. The approach has to consider the solid form of the materials and compatibility of any a...

Determining the selection rules for the interaction of tunneling charge carriers with molecular vibrational modes is important for a complete understanding of charge transport in molecular electronic junctions. Here, we report the low-temperature charge transport characteristics for junctions formed from hexadecanethiol molecules having varying degrees of fluorination. Our results demonstrate t...

Gemcitabine is a fluorinated nucleoside currently administered against a number of cancers. It consists of a cytosine base and a 2-deoxy-2,2-difluororibose sugar. The synthetic challenges associated with the introduction of the fluorine atoms, as well as with nucleobase introduction of 2,2-difluorinated sugars, combined with the requirement to have an efficient process suitable for large scale ...

Fluorination of magnetite (Fe3O4) by NH4HF2 was investigated using simultaneous thermogravimetry and differential thermal analysis (TG-DTA), observing the morphology phase changes scanning electron microscopy with energy dispersive X-ray spectroscopy (SEM-EDS) diffractometry (XRD). The results indicate that fluorination involvement oxygen begins at room temperature, peaks 1784ºC, is completed 2...

We perform a systematic first-principles study of phosphorene in the presence of typical monovalent (hydrogen and fluorine) and divalent (oxygen) impurities. The results of our modeling suggest a decomposition of phosphorene into weakly bonded one-dimensional (1D) chains upon single- and double-side hydrogenation and fluorination. In spite of a sizable quasiparticle band gap (2.29 eV), fully hy...

Based on a literature precedent, preparation of methyl 4-azido-3,4,6-trideoxy-3-fluoro-alpha-D-mannopyranoside (18) was attempted via fluorination of methyl 4-azido-2-O-benzyl-4,6-dideoxy-alpha-D-altropyranoside with diethylaminosulfur trifluoride (DAST). Contrary to expectations, the reaction took place with retention of configuration at the site of the fluorination yielding methyl 4-azido-2-O...

We report the in vivo fluorination of the tryptophan, tyrosine, and phenylalanine residues in a glycosylation-deficient mutant of Candida antarctica lipase B, CalB N74D, expressed in the methylotrophic yeast Pichia pastoris and subsequently segregated into the growth medium. To achieve this, a P. pastoris strain auxotrophic for all three aromatic amino acids was supplemented with 5-fluoro-L-try...