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New Unsymmetrical Zinc‐Phthalocyanine Conjugated with One Azo‐Dye Moiety: Synthesis via Opening the Fused Triazole Ring and Spectral Properties
Author(s) -
Àlvarez Micó Xavier,
Vagin Sergei I.,
Subramanian Lakshminarayanapuram R.,
Ziegler Thomas,
Hanack Michael
Publication year - 2005
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/ejoc.200500237
Subject(s) - chemistry , moiety , solvatochromism , conjugated system , tetrahydrofuran , zinc , triazole , ring (chemistry) , phthalocyanine , proton nmr , photochemistry , dimethylformamide , coupling reaction , nuclear magnetic resonance spectroscopy , polymer chemistry , solvent , stereochemistry , organic chemistry , catalysis , polymer
A new method for the preparation of compounds containing an azo‐dye moiety via opening the activated triazole ring upon coupling with nucleophiles was successfully applied to a mono‐triazole‐fused phthalocyaninato zinc complex 1 . The prepared unsymmetrical zinc‐phthalocyanine 3 conjugated with a 2‐hydroxy‐1‐naphthylazo moiety in the periphery was characterized by means of UV/Vis‐, FTIR‐, 1 H and 13 C NMR spectroscopy, MALDI‐TOF spectrometry, and elemental analysis, and the data support its structure. The assignment of signals in the 1 H and 13 C NMR spectra of compound 3 was based on the data from 2‐D CH‐COSY and HC‐HMBC measurements (C–H coupling across one bond and long‐range H–C coupling). The compound exhibits interesting spectroscopic properties, indicating high acidity of the hydroxy group. This phthalocyanine behaves as a strongly solvatochromic compound and can exist in different forms depending on the concentration and nature of solvent. Additionally, photodecomposition of 3 in chloroform and tetrahydrofuran was found to proceed via different pathways. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)