Substituted phthalocyanides with sulfonyl substituted with amino

Details Substituted phthalocyanides with sulfonyl substituted with amino Substituted phthalocyanides with sulfonyl substituted with amino

1996-09-25

1998-08-11

Shah, Mukund J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540128, 540122, 540139, 359103, C07D47822, C09B 4700

Patent

active

057928606

DESCRIPTION:

BRIEF SUMMARY
This is a 35 U.S.C. 371 of PCT/GB95/00647 filed Mar. 23, 1995.
This invention relates to novel substituted phthalocyanines and to certain uses thereof.
Phthalocyanine has the following formula: ##STR2##
The nomenclature for the numbering of the Benzo portion is also included in the above depiction. Generally substituents in the R.sub.2,3,9,10,16,17,23,24 positions are referred to as peripheral groups and substituents in the R.sub.1,4,8,11,15,18,22,25 positions are referred to as non-peripheral groups.
It is known that some phthalocyanine compounds exhibit liquid crystalline behaviour.
The majority of known liquid crystalline compounds have a generally rod-shaped molecular structure and are often characterised by nematic and/or smectic mesophases. There are, however, a number of known compounds which are characterised by a generally disc-like molecular structure. These compounds are termed discotic compounds, which can be characterised by discotic nematic or columnar mesophase(s).
Discotic compounds can be based on a number of "cores", eg benzene, truxene, metallophthalocyanine, phthalocyanines and triphenylene.
Guillon et al Mol. Cryst. Liq. Cryst.; 1985, vol 130, pp223-229, discuss columnar mesophases from metallated and metal free derivatives of phthalocyanine in which the phthalocyanine is substituted on the benzene rings with various groups all of which are attached to the phthalocyanine core via a CH.sub.2 unit.
Piechocki and Simon; New Journal of Chemistry, vol 9, no 3, 1985, p159-166. report the synthesis of octa-substituted phthalocyanine derivatives forming discotic mesophases. The side chains are linked to the phthalocyanine core via a CH.sub.2 unit.
Most liquid crystal compounds are known as thermotropic liquid crystal compounds. Thermotropic liquid crystals exist in dependence of the temperature in certain temperature intervals. In some cases when different substances are mixed together the mixture can exhibit different phases not only as the temperature is changed, but also as the concentration of one component of the mixture is changed. When the liquid crystal phase is dependent on the concentration of one component in another it is called a lyotropic liquid crystal. The easiest way to make a lyotropic liquid crystal mixture is to start with a molecule that possesses end groups with different properties. For example one end could show an affinity for water and the other end tends to exclude water. Molecules which possess both a hydrophilic group and a part which is a hydrophobic group can display characteristics of both classes, therefore they are called amphiphilic molecules.
Lyotropic liquid crystals have numerous potential applications including detergents, the recovery of oil from porous rocks and in the food industry for example as food emulsifiers. There may also be medical applications for lyotropic liquid crystal systems. For example, amphiphilic materials could help to make drugs more soluble in the blood.
For a review of phthalocyanine thermotropics, see Simon and Bassoul in Phthalocyanines, Properties and Applications, Ed., C. C. Leznoff and A. B. P. Lever. V.C.H. Publishers 1992, p 227.
Some phthalocyanines also absorb radiation in the far-red to near infra-red regions of the electromagnetic spectrum. Compounds which absorb strongly at wavelengths of laser light can in principle be exploited as guest dyes dissolved in liquid crystalline host materials in a laser addressed system.
Materials have been proposed for laser addressed applications in which laser beams are used to scan across the surface of the material or leave a written impression thereon. For various reasons, many of these materials have consisted of organic materials which are at least partially transparent in the visible region. The technique relies upon localised absorption of laser energy which causes localised heating and in turn alters the optical properties of the otherwise transparent material in the region of contact with the laser beam. Thus as the beam traverses the material, a written impression of its path

REFERENCES:
patent: 5348840 (1994-09-01), Sakamoto et al.
patent: 5506708 (1996-04-01), Harrison et al.

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