N-substituted triarylmethane sulfonamides and method of preparat

Details N-substituted triarylmethane sulfonamides and method of preparat N-substituted triarylmethane sulfonamides and method of preparat

1993-06-11

1995-03-21

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540466, 540543, 544 70, 546 15, 548226, 549388, C07D491107, C07D40510, C07D31188, G03C 172

Patent

active

053997093

ABSTRACT:
A novel class of N-substituted triarylmethane sulfonamides is provided which undergo reversible oxidation into colored form and reversible reduction of the oxidized form into colorless form. The N-substituted triarylmethane sulfonamides can be represented by the formulae: ##STR1## wherein B is a carbocyclic ring or rings; T is a 5- or 6-membered ring; Y is a moiety selected from ##STR2## wherein E, positioned ortho or para to said --OH group, is selected from --OH, --NH.sub.2, --NHR', --NR'R" and --NHSO.sub.2 R' wherein R' and R" each are lower alkyl groups having 1 to 6 carbon atoms or aralkyl wherein the aryl portion may be substituted with alkyl groups having 1 to 24 carbon atoms, and E' is hydrogen or a monovalent group that is substituted on one of the remaining carbon atoms; G and G' each are hydroxy or methoxy, provided one is hydroxy and the other is methoxy; and Z and Z' taken individually represent the moieties to complete the chromophoric system of a triarylmethane dye when said N-containing ring, T, is open and Z and Z' taken together represent the bridged moieties to complete the chromophoric system of a bridged triarylmethane dye when said N-containing ring, T, is open; and Y' represents the quinoid form of Y. Preferred embodiments comprise xanthene sulfonamides having N-aryl substituents, e.g., hydroquinone substituents. These compounds possess redox potentials ranging between about +200 to -500 millivolts and thus are useful as dyes for producing photographic, photothermographic, thermal, and pressure-induced images, as well as being useful as redox indicators in a wide variety of biological and chemical reactions.

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