Light-fast, high-capacity optical storage media

A method for the preparation of a compound of formula

• wherein R1 and R11 are each independently of the other(s) hydrogen;
• C1-C24alkyl, C2-C24alkenyl, C2-C24alkynyl, C3-C24cycloalkyl, C3-C24cycloalkenyl or C3-C12heterocycloalkyl each unsubstituted or mono- or poly-substituted by halogen, NO2, CN, NR14R15, NR14R15R16+, NR14COR15, NR16CONR14R15, OR14, SR14, COO−, COOH, COOR14, CHO, CR16OR14OR15, COR14, SO2R14, SO3−, SO3H, SO3R14 or by OSiR16R17R18, or C7-C18aralkyl, C6-C14aryl or C4-C12heteroaryl each unsubstituted or mono- or poly-substituted by halogen, NO2, CN, NR14R15, NR14R15R16+, NR14COR15, NR16CONR14R15, R14, OR14, SR14, CHO, CR16OR14OR15, COR14, SO2R14, SO3−, SO3R14, SO2NR14R15, COO−, COOR14, CONR14R15, PO3−, PO(OR14)(OR15), SiR16R17R18, OSiR16R17R18 or by SiOR16OR17OR18;
• with the proviso that R1 and R11 are not simultaneously hydrogen;
• R2, R3, R9 and R10 are each independently of the others C1-C12alkyl unsubstituted or mono- or poly-substituted by halogen, OR16, SR16, NO2, CN, NR19R20, COO−, COOH, COOR16, SO3−, SO3H or by SO3R16,
• wherein R2 and R3 and/or R9 and R10 may be bonded to one another in pairs, via a direct bond or a bridge —O—, —S— or —NR21—, in such a manner that a 5- to 12-membered ring is formed;
• R4 and R8 are each independently of the other(s) C1-C3alkylene or C2-C3alkenylene each unsubstituted or mono- or poly-substituted by halogen, R21, OR21, SR21, NO2, CN, NR22R23, COO−, COOH, COOR21, SO3−, SO3H or by SO3R21;
• R5, R7, R12 and R13 are each independently of the others hydrogen, halogen, OR24, SR24, NO2 or NR24R25, or C1-C24alkyl, C2-C24alkenyl, C2-C24alkynyl, C3-C24cycloalkyl, C3-C24cycloalkenyl, C3-C12heterocycloalkyl or C7-C18aralkyl each unsubstituted or mono- or poly-substituted by halogen, OR24, SR24, NO2, CN or by NR24R25;
• R6 is hydrogen;
• (CH2)kCOO−, (CH2)kCOOR26, C1-C24alkyl, C2-C24alkenyl, C2-C24alkynyl, C3-C24cycloalkyl or C3-C24cycloalkenyl each unsubstituted or mono- or poly-substituted by halogen, NR26R27 or by OR27;
• or C7-C18aralkyl, C6-C14aryl or C5-C13heteroaryl each unsubstituted or mono- or poly-substituted by halogen, NO2, CN, NR26R27, SO3−, SO3R26, SO2NR26R27, COO−, (CH2)kOR26, (CH2)kOCOR26, COOR26, CONR26R27, OR26, SR26, PO3−, PO(OR26)(OR27) or by SiR16R17R18;
• R14, R15, R19, R20, R21, R22, R23, R24, R25, R26 and R27 are each independently of the others hydrogen;
• C1-C24alkyl, C2-C24alkenyl, C2-C24alkynyl, C3-C24cycloalkyl, C3-C24cycloalkenyl or C3-C12heterocycloalkyl each unsubstituted or mono- or poly-substituted by halogen, NO2, CN, NR16R17, NR16R17R18+, NR16COR17, NR16CONR17R18, OR16, SR16, COO−, COOH, COOR16, CHO, CR16OR17OR18, COR16, SO2R16, SO3−, SO3H, SO3R16 or by OSiR16R17R18;
• or C7-C18aralkyl, C6-C14aryl or C5-C13heteroaryl each unsubstituted or mono- or poly-substituted by halogen, NO2, CN, NR16R17, NR16R17R18+, NR16COR17, NR16CONR17R18, R16, OR16, SR16, CHO, CR16OR17OR18, COR16, SO2R16, SO3−, SO2NR16R17, COO−, COOR18, CONR16R17, PO3−, PO(OR16)(OR17), SiR16R17R18, OSiR16R17R18 or by SiOR16OR17OR18,
• or NR14R15, NR19R20, NR22R23, NR24R25 or NR26R27 is a five- or six-membered heterocycle which may contain an additional N or O atom and may be mono- or poly-substituted by C1-C8alkyl;
• R16, R17 and R18 are each independently of the others hydrogen, C1-C20alkyl, C2-C20alkenyl, C2-C20alkynyl or C7-C18aralkyl, wherein R16 and R17 may be bonded to one another, via a direct bond or a bridge —O—, —S— or —NC1-C8alkyl-, in such a manner that a five-or six-membered ring is formed;
• wherein optionally from 1 to 4 radicals selected from the group consisting of R1, R2, R4, R5, R6, R7, R8, R9, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26 and R27 can be bonded to one another in pairs, via a direct bond or a bridge —O—, —S— or —N(G)-, or separately to Ym− and/or Zn+, G being mono- or poly-substituted C1-C24alkyl, C2-C24alkenyl, C2-C24alkynyl, C3-C24cycloalkyl, C3-C24cycloalkenyl, C3-C12heterocycloalkyl, C7-C18aralkyl, C6-C14aryl or C5-C13heteroaryl;
• Ym− is an organometallic anion;
• Zn+ is a proton or a metal, ammonium or phosphonium cation, or a mixture thereof;
• k is an integer from 1 to 10;
• m, n and o are each independently of the others an integer from 1 to 3;
• and
• p and q are each a number from 0 to 4, the ratio of o, p and q to one another, depending on the charge of the associated sub-structures, being such that there is no excess positive or negative charge in formula (I), (II) or (III);
• in which method a compound of formula M3+Ym−, wherein M3 is Li, Na, K or H3NR6, is added to a compound of formula (I), (II) or (III), wherein Ym− is perchlorate.