# US 5,349,062 A · Substituted naphtho[1,8-de:5,4-d'e']bis[1,3]thiazines, process for their preparation and the use thereof

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- Number: US 5,349,062 A
- Document ID: US5349062A
- Status: Granted
- Kind: A
- Application number: 08/083,814
- Filed: 1993-06-28
- Granted: 1994-09-20
- Earliest claimed: 1992-07-02
- Assignees: Ciba-Geigy Corporation
- Inventors: John Zambounis
- Web page: https://patentgrep.com/patent/US5349062A

## CPC

- C07D 513/06: Peri-condensed systems
- C07C 331/30: containing at least two isothiocyanate groups bound to the same carbon skeleton
- H01B 1/121: {Charge-transfer complexes}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- H01B: CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES (selection for magnetic properties H01F1/00; waveguides H01P {; printed circuits H05K})

## Abstract

Compounds of formula I ##STR1## wherein X.sub.1 and X.sub.2 are each independently of the other O, S or Se, and R.sub.1 and R.sub.2 are each independently of the other a monovalent radical of an aliphatic or aromatic hydrocarbon of 1 to 20 carbon atoms which is unsubstituted or substituted by NH.sub.2, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, phenyl or C.sub.3 -C.sub.8 cycloalkyl. The compounds of formula I are able to form electrically conductive charge transfer complexes.

## Claims

### Claim 1

A compound of formula I ##STR10## wherein X.sub.1 and X.sub.2 are each independently of the other O, S or Se,
and R.sub.1 and R.sub.2 are each independently of the other a monovalent radical of an aliphatic or aromatic hydrocarbon, wherein the aliphatic hydrocarbon radicals are selected from the group consisting of C.sub.1 -C.sub.18 alkyl, C.sub.3 -C.sub.8 cycloalkyl and C.sub.7 -C.sub.12 aralkyl, which aliphatic hydrocarbon radicals are unsubstituted or substituted by NH.sub.2, C.sub.1 -C.sub.6 alkoxy or phenyl, and the aromatic hydrocarbon radicals are selected from the group consisting of C.sub.6 -C.sub.18 aryl, which aromatic hydrocarbon radicals are substituted by NH.sub.2, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or C.sub.3 -C.sub.8 cycloalkyl.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein X.sub.1 and X.sub.2 are identical.

### Claim 3 (depends on 2)

A compound of formula I according to claim 2, wherein X.sub.1 and X.sub.2 are S.

### Claim 4 (depends on 2)

A compound of formula I according to claim 2, wherein X.sub.1 and X.sub.2 are O.

### Claim 5

A charge transfer complex of formula IV
Z.sub.x A.sub.y (IV)
wherein Z is the radical cation of a compound of formula I ##STR11## wherein X.sub.1 and X.sub.2 are each independently of the other O, S or Se,
and R.sub.1 and R.sub.2 are each independently of the other a monovalent radical of an aliphatic or aromatic hydrocarbon, wherein the aliphatic hydrocarbon radicals are selected from the group consisting of C.sub.1 -C.sub.18 alkyl, C.sub.3 -C.sub.8 cycloalkyl and C.sub.7 -C.sub.12 aralkyl, which aliphatic hydrocarbon radicals are unsubstituted or substituted by NH.sub.2, C.sub.1 -C.sub.6 alkoxy or phenyl, and the aromatic hydrocarbon radicals are selected from the group consisting of C.sub.6 -C.sub.18 aryl, which aromatic hydrocarbon radicals are substituted by NH.sub.2, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or C.sub.3 -C.sub.8 cycloalkyl, and A is the anion of an inorganic acid, and 1.ltoreq.x/y.ltoreq.3.

### Claim 6 (depends on 1)

A compound of formula I according to claim 1, wherein the aliphatic hydrocarbon radicals are selected from the group consisting of C.sub.1 -C.sub.12 alkyl, C.sub.4 -C.sub.6 cycloalkyl and C.sub.7 -C.sub.12 aralkyl, and the aromatic hydrocarbon radicals are C.sub.6 -C.sub.12 aryl.

### Claim 7 (depends on 1)

A compound of formula I according to claim 1, wherein R.sub.1 and R.sub.2 are C.sub.1 -C.sub.18 alkyl, unsubstituted or substituted as defined in claim 1, C.sub.5 -C.sub.6 cycloalkyl, phenyl or benzyl.

### Claim 8 (depends on 1)

A compound of formula I according to claim 1, wherein R.sub.1 and R.sub.2 are C.sub.1 -C.sub.12 alkyl, phenyl or benzyl.

### Claim 9 (depends on 1)

A compound of formula I according to claim 1, which is 2',7'-bis(methylthio)naphtho[1,8-de:5,4-d'e']bis[1,3]thiazine.

### Claim 10 (depends on 1)

A compound of formula I according to claim 1, which is 2',7'-bis(methoxy)naphtho[1,8-de:5,4-d'e']bis[1,3]thiazine.

### Claim 11 (depends on 1)

A compound of formula I according to claim 1, which is 2'-methylthio-7'-ethoxynaphtho[1,8-de:5,4-d'e']bis[1,3]thiazine.

### Claim 12 (depends on 1)

A compound of formula I according to claim 1, which is 2'-n-butylthioethylthionaphtho[1,8-de:5,4-d'e']bis[1,3]thiazine.

### Claim 13 (depends on 5)

A charge transfer complex of formula IV as claimed in claim 5, wherein the anion A is selected from the group consisting of F.sup.-, Cl.sup.-, Br.sup.-, I.sup.-, CN.sup.-, OCN.sup.-, SCN.sup.-, SeCN.sup.-, N.sub.3.sup.- I.sub.3.sup.--, I.sub.2 Br.sup.-, IBr.sub.2.sup.-, BrICl.sup.-, Br.sub.3.sup.-, ICl.sub.2.sup.-, CuCl.sub.2.sup.-, CuBr.sub.2.sup.-, AgCl.sub.2.sup.-, AgBr.sub.2.sup.-, AgI.sub.2.sup.-, Ag(CN).sub.2.sup.-, AuCl.sub.2.sup.-, AuBr.sub.2.sup.-, AuI.sub.2.sup.-, Au(CN).sub.2.sup.-, NO.sub.3.sup.-, C(CN).sub.3.sup.-, ClO.sub.4.sup.-, BrO.sub.4.sup.-, IO.sub.4.sup.-, ReO.sub.4.sup.-, FSO.sub.3.sup.-, PO.sub.2 F.sub.2.sup.-, BF.sub.4.sup.-, InBr.sub.4.sup.-, InI.sub.4.sup.-, TlBr.sub.4.sup.-, TlI.sub.4.sup.-, FeCl.sub.4.sup.-, AuCl.sub.4.sup.- , AuBr.sub.4.sup.-, ICl.sub.4.sup.-, SiF.sub.5.sup.-, TeF.sub.5.sup.-, PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, SbCl.sub.6.sup.-, NbF.sub.6.sup.- and TaF.sub.6.sup.-.

### Claim 14 (depends on 5)

A charge transfer complex as claimed in claim 5, which is [2',7'-bis(methylthio)naphtho[1,8-de:5,4-d'e']bis[1,3]thiazino].sub.2 hexafluorophosphate.

### Claim 15 (depends on 5)

A charge transfer complex as claimed in claim 5, which is [2',7'-bis(methylthio)naphtho[1,8-de:5,4-d'e']bis[1,3]thiazino](I.sub.3).s ub.0.46.