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

• Published in: Synthetic communications Vol. 43; no. 9; pp. 1219 - 1228
• Main Authors: Dadapeer, E., Krishna, B. Satheesh, Raju, C. Naga
• Format: Journal Article
• Language: English
• Published: Philadelphia Taylor & Francis Group 03-05-2013; Taylor & Francis Ltd
• Subjects: 1,5-Diaminonaphthalene; Desorption; facile divergent synthesis; Ions; Lasers; Mass spectrometry; Phosphorus; phosphorus-containing dendron; Schiff's condensation; TGA/DTA analysis
• ISSN: 0039-7911; 1532-2432
• DOI: 10.1080/00397911.2011.628773

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 POCl
3
, 3-hydroxy-benzaldehyde, 4-hydroxy-benzaldehyde, and 3-amino-phenol iteratively. The structures of intermediate dendrons were characterized by infrared, NMR (
1
H,
13
C, and
31
P), liquid chromatography-mass spectrometry, and C, H, N analysis. The structure of the final dendron (6) was confirmed by infrared, NMR (
1
H,
13
C, and
31
P), 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.