Synthesis of fluorescent carboxylic acid ligands for construction of monolayers on nanostructures

Two new long-chain carboxylic acids (1, 2) bearing strong fluorescent group pyrene as ligands for Self-Assembled Monolayers (SAMs) have been synthesized. The multistep targeted synthesis is accomplished by use of Pyren-1-yl methylamine hydrochloride and employing simplified synthetic protocols. Compound 2 contains a chiral center purposely introduced along the atom chain in order to make it suitable for chiro-optical studies of the resulting SAMs.

Mannich Bases as Synthetic Intermediates: Alkylation of Amines and Diamines with Bis-ketonic Mannich Bases

The bis-ketonic Mannich base, N,N-bis(β -benzoylethyl)methylamine hydrochloride (1) reacts with primary arylamines and diamines to give ketonic sec-arylamines 3a - e and 4. The piperidines 7a - c were obtained from 1 and primary alkylamines, whereas the 1,4-diazepine derivative 10 was obtained from 1 and ethylenediamine. Treatment of the bis-base 1,4-di[β -(N-morpholino)propionyl]benzene bis(hydrochloride) (11) with primary arylamines gave the corresponding bis-(sec-arylamines) 12a - b, whereas its reaction with ophenylenediamine afforded the bis[1,5-benzodiazepine] ring system 14. The synthesis of the diazacyclophane ring system 15 has been achieved by treating 11 with piperazine. Attempted synthesis of 4- aza-[7]-paracyclophane (16) from 11 and benzylamine led to 17. The reaction of 1 or 11 with phenylhydrazine gave the 2-pyrazolines 18 and 19. Treatment of 3 or 4 with phenylhydrazine and formaldehyde afforded the 2H-1,2,4-triazepines 20a - c and the bis[2H-1,2,4-triazepine] ring system 21.

Powder diffraction investigations of some organic hydrochlorides

Amantadine hydrochloride, p-aminophenol hydrochloride, and methylamine hydrochloride, compounds often studied in pharmacology, were investigated by means of powder diffractometry. The chemical formula of the first compound is C10H17N HCl and crystallizes in the monoclinic system, space group C2∕c (15) with lattice parameters a=2.0279(6) nm, b=1.1171(2) nm, c=9.759(4) nm, and β=109.00(3)°. p-Aminophenol hydrochloride C6H7NO HCl crystallizes in the orthorhombic system, space group P222 with lattice parameters a=0.6619(2) nm, b=0.88461(2) nm, and c=0.6101(2) nm. Methylamine hydrochloride CH5N∙HCl crystallizes in the tetragonal system, space group P4∕nmm (129) with lattice parameters a=b=0.6068(1) nm and c=0.50689(8) nm.