Routes to trans A,B-substituted bacteriochlorins
Bacteriochlorin of Formula I: wherein R is H or silyl are described, along with compositions containing the same and methods of making and using the same.
1. A bacteriochlorin of Formula I:
wherein:
R is H or silyl;
each Wand R 2 is independently selected from the group consisting of H, alkyl, aryl, alkoxy, halo, mercapto, cyano, hydroxyl, nitro, acyl, alkylthio, alkylamino, acyloxy, and —C(O)NR a R b where R a and R b are each independently selected from the group consisting of alkyl, cycloalkyl, alkenyl, alkynyl and aryl, preferably H or alkyl;
each R 3 and R 4 is independently selected from the group consisting of alkyl, cycloalkyl, aryl, and arylalkyl;
each R 5 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, alkoxy, halo, cyano, nitro, acyl, alkylthio, alkylamino, arylalkylamino, disubstituted amino, acylamino, acyloxy, and —C(O)NR a R b where R a and R b are each independently selected from the group consisting of alkyl, cycloalkyl, alkenyl, alkynyl and aryl;
each R 6 and R 7 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, halo, cyano, nitro, acyl, alkoxy, alkylthio, alkylamino, arylalkylamino, disubstituted amino, acylamino, acyloxy, —C(O)NR a R b where R a and R b are each independently selected from the group consisting of alkyl, cycloalkyl, alkenyl, alkynyl and aryl, —C(O)OR c where R c is selected from the group consisting of alkyl, cycloalkyl, alkenyl, alkynyl, aryl, and C(O)OH; and
Z is H or halo.
2. The compound of claim 1 , wherein each R 1 and R 2 is independently selected from the group consisting of H and alkyl.
3. The compound of claim 1 , wherein each R 3 and R 4 is independently selected alkyl.
4. The compound of claim 1 , wherein each R 5 is H.
5. The compound of claim 1 , wherein each R 6 is methylphenyl.
6. The compound of claim 1 , wherein each R 7 is H.
7. The compound of claim 1 , wherein Z is H.
8. The compound of claim 1 , wherein Z is halo.
9. The compound of claim 1 , wherein R is silyl.
10. The compound of claim 1 selected from the group consisting of:
11. The compound of claim 1 , wherein R is trialkylsilyl.
12. The compound of claim 11 , wherein Z is H.
13. A method of making a bacteriochlorin of claim 1 , comprising:
condensing a pair of compounds of Formula II:
wherein each R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is as given above;
in the presence of CF 3 SO 3 R wherein R is silyl, to produce said bacteriochlorin of claim 1 wherein R is silyl.
14. The method of claim 13 , further comprising the step of cleaving said silyl to produce said bacteriochlorin of claim 1 wherein R is H.
15. The method of claim 13 , further comprising the step of halogenating said bacteriochlorin to produce a bacteriochlorin of claim 1 wherein Z is halo.