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Synthesis and Characterization of Soluble Chloro‐ and Aryl(naphthalocyaninato)indium(III) Complexes and Their Precursors
Author(s) -
Schneider Thorsten,
Heckmann Heino,
Barthel Markus,
Hanack Michael
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200108)2001:16<3055::aid-ejoc3055>3.0.co;2-e
Subject(s) - chemistry , indium , steric effects , trifluoromethyl , aryl , carbon 13 nmr , characterization (materials science) , stereochemistry , medicinal chemistry , organic chemistry , alkyl , nanotechnology , materials science
The syntheses of highly soluble chloro(naphthalocyaninato)indium(III) compounds (R 2 ) 4 (R 4 ) 4 NcInCl ( 5a : R 2 = H, R 4 = tert ‐butyl; 6a : R 2 = R 4 = tert ‐butyl; 7a : R 2 = 2‐ethylhexyloxy, R 4 = tert ‐butyl; 8a : R 2 = R 4 = 2‐ethylhexyloxy), and their reactions with R′MgBr [ b : R′ = p ‐(trifluoromethyl)phenyl; c : R′ = pentafluorophenyl] producing the axially substituted aryl(naphthalocyaninato)indium(III) compounds 5b , 5c , 6b , 6c , 7b , 7c , 8b , and 8c are described. All compounds were characterized by IR, UV/Vis, MS, and 1 H, 13 C, and 19 F NMR, as well as by elemental analysis. The high solubilities of the octasubstituted naphthalocyanines 6 − 8 and their low tendencies to form aggregates are due to steric crowding arising from the new unsymmetrical peripheral substitution pattern and the bulky, electron‐withdrawing axial ligands. These properties make the (naphthalocyaninato)indium compounds very interesting candidates for further investigations concerning their nonlinear optical properties, particularly for optical limiting applications. We also report on the complete syntheses and characterization of the corresponding diiminoisoindoline precursors 2 (R 2 = R 4 = tert ‐butyl), 3 (R 2 = 2‐ethylhexyloxy; R 4 = tert ‐butyl) and 4 (R 2 = R 4 = 2‐ethylhexyloxy).