Cyanine dye having multifunctional peripheral groups
The present invention provides an IR-absorbing dye of formula (I) or (II) wherein R 10 , R 13 , R 20 , R 23 , R 30 , R 33 , R 40 and R 43 are independently selected from a C 1-12 alkyl group bearing a hydrophilic or hydrophilizable group; R 11 , R 12 , R 21 , R 22 , R 31 , R 32 , R 41 and R 42 are independently selected from H or a C 1-30 hydrocarbyl group, or each of R 11 /R 12 , R 21 /R 22 , R 31 /R 32 , and R 41 /R 42 are together joined to form a C 3-30 hydrocarbylene group; M is selected from Si(A 1 )(A 2 ), Ge(A 1 )(A 2 ), Ga(A 1 ), Mg, Al(A 1 ), TiO, Ti(A 1 )(A 2 ), ZrO, Zr(A 1 )(A 2 ), VO, V(A 1 )(A 2 ), Mn, Mn(A 1 ), Fe, Fe(A 1 ), Co, Ni, Cu, Zn, Sn, Sn(A 1 )(A 2 ), Pb, Pb(A 1 )(A 2 ), Pd and Pt; A 1 and A 2 are axial ligands, which may be the same or different, and are selected from —OH, halogen, —OR 3 , a hydrophilic ligand and/or a ligand suitable for reducing intermolecular interactions; R 3 is a selected from C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl or Si(R x )(R y )(R z ); and R x , R y and R z may be the same or different and are selected from C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl, C 1-12 alkoxy, C 5-12 aryloxy or C 5-12 arylalkoxy. Dyes of this type are especially suitable for use in netpage and Hyperlabel systems.
1. A IR-absorbing dye of formula (I) or (II)
wherein
R 10 , R 13 , R 20 , R 23 , R 30 , R 33 , R 40 and R 43 are independently selected from a C 1-12 alkyl group bearing a hydroxyl or protected hydroxyl group;
each of R 11 /R 12 , R 21 /R 22 , R 31 /R 32 , and R 41 /R 42 are together joined form
T is selected from a substituent comprising a polymeric chain or a C 1-30 hydrocarbyl group;
W is —SO 3 H or a water-soluble salt thereof;
m is 0, 1 or 2;
n is 0, 1 or 2;
M is selected from Si(A 1 )(A 2 ), Ge(A 1 )(A 2 ), Ga(A 1 ), Mg, Al(A 1 ), TiO, Ti(A 1 )(A 2 ), ZrO, Zr(A 1 )(A 2 ), VO, V(A 1 )(A 2 ), Mn, Mn(A 1 ), Fe, Fe(A 1 ), Co, Ni, Cu, Zn, Sn, Sn(A 1 )(A 2 ), Pb, Pb(A 1 )(A 2 ), Pd and Pt;
A 1 and A 2 are axial ligands, which may be the same or different, and are selected from OH, halogen or OR 3 ;
R 3 is a selected from C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl or Si(R x )(R y )(R z ); and
R x , R y and R z may be the same or different and are selected from C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl, C 1-12 alkoxy, C 5-12 aryloxy or C 5-12 arylalkoxy.
2. The dye of claim 1 , wherein R 10 , R 13 , R 20 , R 23 , R 30 , R 33 , R 40 and R 43 are selected from —(CH 2 ) 4 OH, —(CH 2 ) 4 OTBDMS, —(CH 2 ) 4 OTHP or —(CH 2 ) 4 OBz.
3. The dye of claim 1 , wherein R 10 , R 13 , R 20 , R 23 , R 30 , R 33 , R 40 and R 43 are all the same.
4. The dye of claim 1 , wherein each of R 11 /R 12 , R 21 /R 22 , R 31 /R 32 , and R 41 /R 42 is the same.
5. The dye of claim 1 , wherein M is Si(A 1 )(A 2 ), Ge(A 1 )(A 2 ), Ga(A 1 ), Al(A 1 ), Mn(A 1 ), Fe(A 1 ) or Sn(A 1 )(A 2 ).