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Chloro boron subphthalocyanine and its derivatives: dyes , pigments or somewhere in between?

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Paton, Andrew S. Lough, Alan Morse, Graham E. Bender, Timothy P.
Description	Author Affiliation: Morse GE ( Department of Chemical Engineering & Applied Chemistry, University of Toronto, 200 College Street, M5S 3E5, Toronto, Canada.)
Abstract	Nine derivatives of chloro boron subphthalocyanine ( Cl-BsubPc , 1) have been synthesized and characterized. Seven dimers of Cl-BsubPc have been synthesized by reaction with biphenol (2a), bisphenol A (2b), bisphenol F (2c), bisphenol O (2d), bisphenol P (2e), bisphenol S (2f) and bisphenol Z (2g). For comparison two monomeric phenoxy - (3a) and 4-methylphenoxy (3b) BsubPcs have also been synthesized. Crystals were grown for dimer 2c, whereas all attempts to grow crystals of the remaining dimers resulted in the formation of molecular glasses or amorphous precipitates. Analysis on the structure of 2c suggests that the rigidity and aromatic nature of the central bisphenolic directs the crystal packing. The solubility of the BsubPc dimers in a variety of common organic solvents was measured and compared to that of Cl-BsubPc (1) and monomers 3a and 3b. We have defined ranges for classifying BsubPc derivatives based on their solubility in these solvents : pigment ≤ 1 × $10^{−8}$ M, 1 × $10^{−3}$ M ≤ pigment-like > 1 × $10^{−8}$ M, 1 × $10^{−2}$ M ≤ dye -like > 1 × $10^{−3}$ M, and dye > 1 × $10^{−2}$ M. From this Cl-BsubPc (1) and compounds 2a, 2b, 2c, 2e and 2g are pigment-like while compounds 2d, 2f, 3a and 3b are dye -like. None are exclusively pigments or dyes . In this first approximation of this dye versus pigment classification we have not considered other processes besides solvation which could be undesirable such as polymorphic changes or Ostwald ripening . We have concluded that derivatization of Cl-BsubPc (1) with bisphenols and phenols can be used to control the solubility of BsubPc derivatives. We have also concluded that Cl-BsubPc (1) should not be considered a dye rather is pigment-like in its solubility.
ISSN	14779226
Issue Number	16
Journal	Dalton Trans.
Volume Number	39
e-ISSN	13645447
Language	English
Publisher	Royal Society of Chemistry
Publisher Date	2010-04-28
Publisher Place	Great Britain (UK)
Access Restriction	Subscribed
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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