Substituted tetrathiotetracenes and tetraselenotetracenes

    公开(公告)号:US4981962A

    公开(公告)日:1991-01-01

    申请号:US356824

    申请日:1989-05-24

    Abstract: Substituted tetrathiotetracenes and tetraselenotetracenes of the formula I ##STR1## in which Z is --S-- or --Se-- and (a) R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are H and R.sup.5 to R.sup.8 are each H and at least one of the radicals R.sup.5 to R.sup.8 independently of one another is a substituent belonging to the group comprising C.sub.1 -C.sub.20 alkyl--X--.sub.p which is unsubstituted or substituted by halogen, --CN, --CONR.sup.9 R.sup.10, --OR.sup.9, --SR.sup.9 or --COOR.sup.9, with the exception of C.sub.1 -C.sub.4 alkyl and methoxy, C.sub.2 -C.sub.18 alkenyl--X--.sub.p, C.sub.2 -C.sub.18 -alkynyl--X--.sub.p, C.sub.3 -C.sub.8 cycloalkyl--X--.sub.p, (C.sub.1 -C.sub.12 alkyl)--C.sub.3 -C.sub.8 cycloalkyl--X--.sub.p, C.sub.3 -C.sub.8 cycloalkyl-C.sub.r H.sub.2r --X--.sub.p, (C.sub.1 -C.sub.12 alkyl)-C.sub.3 -C.sub.8 -cyclo alkyl-C.sub.r H.sub.2r --X--.sub.p, phenyl--X--.sub.p, (C.sub.1 -C.sub.12)alkyl)-phenyl--X--, phenyl-C.sub.r H.sub. 2r --X--.sub.p and (C.sub.1 -C.sub.12 alkyl)-phenyl-C.sub.r H.sub.2r --X--.sub.p, r is 1 or 2 and p is 0 or 1 and X is --O--, --S--, --SO-- or --SO.sub.2 --, or R.sup.5 to R.sup.8 independently are a substituent belonging to the group comprising --Br, --CF.sub.3, --CN, --Si(C.sub.1 -C.sub.4 alkyl).sub.3, --S--(C.sub.m H.sub.2m O)--.sub.n R.sup.11 or --O--C.sub.m H.sub.2m --O--R.sup.11, or each one of R.sup.5 to R.sup.8 is --F or --Cl and at least one further member of R.sup.5 to R.sup.8 is a substituent of the groups defined above, including C.sub.1 -C.sub.4 alkyl and methoxy, R.sup.9 and R.sup.10 independently of one another are H, C.sub.1 -C.sub.12 alkyl, phenyl or --C.sub.m H.sub.2m --O--.sub.q R.sup.11, or R.sup.9 and R.sup.10 together are tetramethylene, pentamethylene, 3-oxapentylene or --CH.sub.2 CH.sub.2 NR.sup.9 CH.sub.2 CH.sub.2 --, R.sup.11 is H or C.sub.1 -C.sub.12 -alkyl, m is a number from 2 to 4, n is a number from 2 to 20 and q is a number from 1 to 20, orb) R.sup.1 to R.sup.8 independently of one another are H or one of the substituents defined above, including C.sub.1 -C.sub.4 alkyl and methoxy, or --COOR.sup.9 or --CONR.sup.9 R.sup.10 or two pairs of adjacent radicals of R.sup.1 to R.sup.8 are --CO--O--CO-- or --CO--NR.sup.9 --CO--, and at least one of R.sup.1 to R.sup.4 and also R.sup.5 to R.sup.8 is a substituent, with the exception of R.sup.2, R.sup.3, R.sup.6 and R.sup.7 when these are --F and methyl, and where R.sup.9 and R.sup.10 are as defined above.With electron acceptors they form charge-transfer complexes which can be used as organic electrical conductors, displays, optical switches and sensors.

    Process for producing 3,4,9,10-tetrathioperylene and
3,4,9,10-tetraselenoperylene
    5.
    发明授权
    Process for producing 3,4,9,10-tetrathioperylene and 3,4,9,10-tetraselenoperylene 失效
    制备3,4,9,10-四硫杂环戊烯和3,4,9,10-四硒代环戊烯的方法

    公开(公告)号:US4505858A

    公开(公告)日:1985-03-19

    申请号:US538022

    申请日:1983-09-30

    Applicant: Carl W. Mayer

    Inventor: Carl W. Mayer

    CPC classification number: C07D495/06 C07D517/06 C07D517/08

    Abstract: Chalcogen-substituted perylenes of the formula I ##STR1## wherein X is S or Se can be obtained in a simple manner, under mild reaction conditions and in pure form by heating a compound of the formula II ##STR2## in nitrobenzene, or in a mixture of nitrobenzene and an organic solvent miscible therewith and inert under the reaction conditions, in the presence of a Lewis acid or a protonic acid at 20.degree. to 120.degree. C. The perylenes of the formula I are used for example as donors for the production of organic conductors or semiconductors (charge-transfer-salts).

    Abstract translation: 可以在温和的反应条件下以简单的方式获得其中X为S或Se的式I化合物(I)的硫族原子取代的二萘嵌苯,并且通过加热式II化合物(II) 在硝基苯中,或在硝基苯和可与之混合的有机溶剂的混合物中,在反应条件下,在路易斯酸或质子酸存在下,在20-120℃下,将式I的苝用于 例如作为生产有机导体或半导体(电荷转移盐)的供体。

Patent Agency Ranking