2. Phalocyanines are a work horse in the dye industry,
discovered back in 1907 by accident by Braun and
Tcherniac who recorded a highly coloured compound
after heating ortho-cyanobenzamide at high
temperature.
It was fully structurally characterised by the end of
world war one by Reginald and his students, who used
different techniques including elemental analysis,
ebullioscopic molecular determination and oxidative
degradation in order to obtain the structure of
phthalocyanine.
3. And this was proven by Prof J Robertson and co-
workers at the Davy Faraday laboratory in 1930 via X-
ray diffraction techniques. However, the identification
of the components of the mixture was not possible back
then. This was made possible by the invention of 1H
NMR and 13C NMR.
5. Any transition metal can be put in the centre
Radioactive metal if required
Pcs typically absorbed in about 620-700nm which is
not bad but the problem with Pcs is they aggregate in
solution, so when molecules aggregate their photo
physical properties change. They’re not good basically,
you kill it.
6. An important characteristic in organic molecules is that
the physical and chemical properties of the molecules
can be altered by changing the molecular structure.
substituted and unsubstituted Pc
Fluorinated Pcs are highly stable and an excellent
catalyst for photooxygenation.
7. Enrichment of photo-sensitizer
Photo-stability
High level of oxygen production
Lipophilicity
Selective accumulation in tumour cells
Photo-dynamic therapy agent
As an excellent probe for sensitive and minimally all-
encompassing imaging
HOMO & LUMO increases
8. 15% yield was obtained with a melting point
of 70 - 72oC which is 22oC more than the
literature value of 48 - 49oC
NC
NC O
4 butoxy phthalonitrile
CN
CN
O2N
4-Nitrophthalonitrile
Butanol
DMF and K2CO3
CH3
9. NC
NC O
Butanol
DMF and K2CO3
CN
CN
F
F
F
F
Tetrafluorophthalonitrile
F
F
F
4-Butoxy-3,5,6-trifluoro-phthalonitrile
CH3
(4-Amino-butyl)-carbamic acid tert-butyl
ester Amine (A)
N
N
HH
H
O
O C
CH3
CH3
CH3
10. H2N
Ethylenediamine Amine (B)
MW 60.10g/mol
BOC2O
O
O
N
H
C
NH2
NH2
MW 218.25g/mol
(2-Amino-ethyl)-carbamic acid tert-butyl ester
MW 160.214g/mol
C O
O
O
O
C
11. NH2N
(3-Amino-propyl)-carbamic acid tert-butyl ester Amine (D)
MW= 174g/mol
K2CO3
DMF
Tetrafluorophthalonitrile
CN
CN
F
F
F
HN
O
O
4-(3,4-Dicyano-2,5,6-trifluoro-phenylamino)-butyric acid tert-butyl ester
HN
O
O C
CH3
CH3
CH3
H
