Synthesis, Characterization, and Thermogravimetric Studies of a Phosphorus-Containing Dendron Built from 1,5-Diaminonaphthalene at the Core

Abstract

A facile divergent synthesis of a phosphorus-containing dendron containing 1,5-diaminonaphthalene is described. The phosphorus-containing dendron, functionalized with a 1,5-diaminonaphthalene unit at the core and phenolic OH groups grafted at the periphery, has been accomplished in a versatile, simple fashion, using Schiff's condensation and nucleophilic substitution reactions with POCl₃, 3-hydroxy-benzaldehyde, 4-hydroxy-benzaldehyde, and 3-amino-phenol iteratively. The structures of intermediate dendrons were characterized by infrared, NMR (¹H, ¹³C, and ³¹P), liquid chromatography–mass spectrometry, and C, H, N analysis. The structure of the final dendron (6) was confirmed by infrared, NMR (¹H, ¹³C, and ³¹P), matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, and C, H, N analysis. The thermal stability and degradation of the resulting final dendron was checked by thermal gravitometric analysis/differential thermal analysis.

GRAPHICAL ABSTRACT

Keywords:

• 1,5-Diaminonaphthalene
• facile divergent synthesis
• phosphorus-containing dendron
• Schiff's condensation
• TGA/DTA analysis

ACKNOWLEDGMENT

The authors thank Human Resource Development Group, Council of Scientific and Industrial Research, New Delhi, India, for sanctioning a major research project [No. 01(2309)/09/EMR-II].