Substituted tetrathiotetracenes and tetraselenotetracenes

Details Substituted tetrathiotetracenes and tetraselenotetracenes Substituted tetrathiotetracenes and tetraselenotetracenes

C - Chemistry, Metallurgy

07

D

260/349, 260/279

C07D 495/06 (2006.01) B05D 1/20 (2006.01) C07D 517/06 (2006.01) C07F 7/08 (2006.01) C08G 61/12 (2006.01) C09K 9/02 (2006.01) H01B 1/12 (2006.01)

Patent

CA 1336606

Substituted tetrathiotetracenes and tetraselenotetracenes of the formula I Image (I), in which Z is -S- or -Se- and a) R1, R2, R3 and R4 are H and R5 to R8 are each H and at least one of the radicals R5 to R8 independently of one another is a substituent belonging to the group comprising C1-C20alkyl?X? which is unsubstitu- ted or substituted by halogen, -CN, -CONR9R10, -OR9, -SR9 or -COOR9, with the exception of C1-C4alkyl and methoxy, C2-C18alkenyl?X?, C2-C18- alkynyl?X?, C3-C8cycloalkyl?X?, (C1-C12alkyl)-C3-C8cyclo- alkyl?X?, C3-C8cycloalkyl-CrH2r?X?, (C1-C12alkyl)-C3-C8-cyclo alkyl-CrH2r?X?-, phenyl?X?, (C1-C12)alkyl)-phenyl?X?, phenyl-CrH2r?X? and (C1-C12alkyl)-phenyl-CrH2r?X?, r is 1 or 2 and p is 0 or 1 and X is -O-, -S-, -SO- or -SO2-, or R5 to R8 independently are a substituent belonging to the group comprising -Br, -CF3, -CN, -Si(C1-C4alkyl)3, -S-(CmH2m? or -O?CmH2m-?, or each one of R5 to R8 is -F or -Cl and at least one further member of R5 to R8 is a substituent of the groups defined above, including C1-C4alkyl and methoxy, R9 and R10 independently of one another are H, C1-C12alkyl, phenyl or ?CmH2m-O?, or R9 and R10 together are tetramethylene, pentamethylene, 3-oxapentylene or -CH2CH2NR9CH2CH2-, R11 is H or C1-C12- 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, or b) R1 to R8 independently of one another are H or one of the substituents defined above, including C1-C4alkyl and methoxy, or -COOR9 or -CONR9R10 or two pairs of adjacent radicals of R1 to R8 are -CO-O-CO- or -CO-NR9-CO-, and at least one of R1 to R4 and also R5 to R8 is a sub- stituent, with the exception of R2, R3, R6 and R7 when these are -F and methyl, and where R9 and R10 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.

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