ИСТИНА |
Войти в систему Регистрация |
|
ФНКЦ РР |
||
Macrocyclic compounds containing C2-chiral fragment of (S)-1,1’-binaphthalene-2,2’-diamine (BINAM) and aromatic spacers like 1,3-disubstituted benzene, 2,7-disubstituted naphthalene, oxadiamine linkers with different number of oxygen atoms were synthesized via Pd(0)-catalyzed amination reactions [1]. The syntheses of the N,N’-diaryl substituted BINAM 1 and 7 were run in the presence of Pd(dba)2/Xantphos (Xantphos = 4,5-bis(diphenylphosphino)-9,9-dimethylxantene), and macrocyclization reactions were catalyzed by Pd(dba)2/DavePhos or Pd(dba)2/BINAP (DavePhos = 2-dimethylamino-2’-dicyclohexylphosphinobiphenyl, BINAP= 2,2’-bis(diphenylphosphino)-1,1’-binaphthalene). The best yield of the macrocycles 2-6 with the phenylene spacer reached 53%, those with naphthalene spacer 8-11 – 34%, and those with benzyl spacer 13-15 – 45%. Macrocycle 5 containing phenylene spacer and trioxadiamine linker possesses the fluorescence with the emission maximum at 490 nm, and in the presence of (S)-(+)-2-phenylglycinol a certain enhance of the emission with the hypsochromic shift of the maximum was observed. No changes were noted either in the presence of its isomer, (R)-(-)-2-phenylglycinol, or in the presence of other chiral amino alcohols like (S)- and (R)-2-amino-3-methyl-1-buthanol (L-and D-valinol), (S)-2-amino-1-propanol, (1S)-(2R)-2-amino-1,2-diphenylethanol.