The solubilities of tetra(monofluorophenyl) porphines

INORG.

NUCL.

CHEM.

LETTERS

Vol. 9, pp. 1219-1220, 1973.

Pergamon Press. Printed in Great Britain.

THE SOLUBILITIES OF TETRA( MONOFLUOROPHENYL ) PORPHINES E. B. F l e i s c h e r ~, R. Foust, D. J e t e r and R. Near C h e m i s t r y Department, University of California, Irvine, California 92664 (Received 16 July 1973)

Summary.

The solubilities of s e v e r a l tetra( monofluorophenyl)porphines

have been d e t e r m i n e d in s e v e r a l organic solvents; the m e t a - f l u o r o derivative is v e r y soluble c o m p a r e d to the other compounds studied.

In chloroform the

m - F - T P P has a solubility at 300 o f . 21 M which is about 104 t i m e s m o r e soluble than p - F - T P P . The wide employment of substituted tetraphenylporphines in the chemical and physical studies of porphyrins and metalloporphyrins p r o m p t s us to r e p o r t a r a t h e r interesting and useful observation concerning the solubility of some of these porphyrins.

The low solubility of many of these

porphyrins make their study s o m e t i m e s difficult.

We have determined the

solubility of meso-tetraphenylporphine ( T P P ) and the three monofluorophenyl d e r i v a t i v e s of T P P , the o - F - T P P ,

m-F-TPP,

solvents pyridine, benzene, and chloroform.

and p - F - T P P in the

The above compounds w e r e

synthesized and purified by previous l i t e r a t u r e methods. 1 The m e a s u r e d solubilities a r e given in the Table. ing these porphyrin solubilities.

T h e r e a r e two points of interest concern-

F i r s t l y , the r e l a t i v e l y high solubility of the

m - F - T P P derivative will make many porphyrin studies much e a s i e r than before; secondly, the large difference in the solubility of m - F - T P P as c o m p a r e d to the p - F - T P P (. 21 M compared to 4 . 8 x 10-5 M ) a p p e a r s unusual and not e a s i l y explicable. 1219

1220

SOLUBILITIES

VoL 9, No. U

TABLE Molar Solubilities of Some P o r p h y r i n s at 30°C

Compound TPP

P y r idine 9.7 x

lO'3M

Benzene

Chloroform

7.0x

10"3M

3.6 x

10-2M

m-F-TPP

1.2 x 10"IM

3.8 x

10-2M

2. l x 10"IM

o-F-TPP

1.1 x 10-2M

2. 1 x

10-3M

9.0 x

10"3M

p-F-TPP

7. l x 10"5M

4. 8 x

10"5M

4.9 x

10"5M

REFERENCES

1)

A. Adler, F. Longo, J. Finarelli, J. Goldmacher, J. Assour, and L. Korsakoff, J . Org. Chem. ~ ~

476 ( 1967 ) ; J. Kim,

J. Leonard, and F. Longo, J_.. Amer. Chem. Soc.~

~

3986

( 1972 ).

2)

This work was supported by Grants from the National Institute of Health.