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Studies on Properties of p ‐Nitrophenylazo Calix[4]arene Derivatives
Author(s) -
ChuanMing Jin,
GuoYuan Lu,
XiaoZeng You,
Xun Guo,
MinZbi Gui,
Hong Zhang
Publication year - 2003
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20030210203
Subject(s) - chemistry , diazo , hyperpolarizability , calixarene , monolayer , medicinal chemistry , nitro , phenol , crystallography , alkyl , stereochemistry , organic chemistry , molecule , biochemistry , polarizability
The p ‐nitrophenylazo calix[4]arene derivatives 1a‐1d with nonlinear optical (NLO) properties were prepared by the diazo‐coupling reaction of calix[4]arene with p ‐nitrophenyl diazonium. The diazotization reaction of p ‐nitroaniline was carried out with isoamyl nitrite as a source of nitrous add in EtONa/EtOH under refluxing condition. X‐Ray crystallographic analysis and 1 H NMR spectra reveal that they exist as cone conformation in crystal state or in solution. HRS measurements at 1064 nm in THF indicate that p ‐nitro‐phenylazo calix[4]arenes have higher hyperpolarizability β z values than the corresponding reference compound 4‐(4‐nitrophenylazo)‐2, 6‐dimethyl‐phenol, without red shift of the charge transfer band. The tetrakis p ‐nitrophenylazo calix[4]arene (2) with longer alkyl chains can form monolayer at the air/water interface.