De novo synthesis of bacteriochlorins
A method of making a bacteriochlorin is carried out by condensing a pair of compounds of Formula II to produce the bacteriochlorin, wherein R is an acetal or aldehyde group. The condensing may be carried out in an organic solvent, preferably in the presence of an acid. The bacteriochlorins are useful for a variety of purposes such as active agents in photodynamic therapy, luminescent compounds in flow cytometry, solar cells, light harvesting arrays, and molecular memory devices.
1. A compound of Formula I:
wherein:
M is a metal or is absent;
X is NH;
R 1 and R 2 are each 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;
R 5 is 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; and
R 6 and R 7 are each 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 and aryl, and C(O)OH.
2. The compound of claim 1 , wherein:
R 1 , R 2 , R 5 , R 7 and R 8 are each H;
R 3 and R 4 are each alkyl; and
R 6 is optionally substituted aryl.
3. The compound of claim 2 , wherein:
R 1 , R 2 , R 5 , R 7 and R 8 are each H;
R 3 and R 4 are each methyl; and
R 6 is p-tolyl.
4. The compound of claim 1 , wherein M is present and is selected from the group consisting of Pd, Pt, Mg, Zn, Al, Ga, In, Sn, Cu, Ni, and Au.
5. A composition consisting of a compound of claim 1 , wherein:
said composition has a peak molar absorption coefficient in solution of 10,000 to 300,000 M −1 cm −1 at a wavelength between 650 and 900 nanometers; and
said composition has a loss of not more than 20 percent of said compound when stored in a sealed vessel at room temperature in the absence of ambient light for at least 3 months.
6. A composition comprising a compound of claim 1 in a solvent, wherein
said composition has a peak molar absorption coefficient in solution of 10,000 to 300,000 M −1 cm −1 at a wavelength between 650 and 900 nanometers; and
said composition has a loss of not more than 20 percent of said compound when stored in a sealed vessel at room temperature in the absence of ambient light for at least 3 months.
7. A pharmaceutical composition comprising a compound of claim 1 in a pharmaceutically acceptable carrier.
8. The composition of claim 7 , wherein said carrier comprises an aqueous carrier.
9. The composition of claim 7 , wherein said carrier comprises an organic solvent.
10. The composition of claim 7 , wherein:
said composition has a peak molar absorption coefficient in solution of 10,000 to 300,000 M −1 cm −1 at a wavelength between 650 and 900 nanometers; and
said composition has a loss of not more than 20 percent of said compound when stored in a sealed vessel at room temperature in the absence of ambient light for at least 3 months.