Convergent synthesis of multiporphyrin light-harvesting rods
AssigneeNorth Carolina State University
InventorsJonathan S. Lindsey, Robert S. Loewe
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Abstract
The present invention provides a convergent method for the synthesis of light harvesting rods. The rods are oligomers of the formula A1(Ab+1)b, wherein b is at least 1, A1 through Ab+1 are covalently coupled rod segments, and each rod segment A1 through A1+b comprises a compound of the formula X1(Xm+1)m wherein m is at least 1 and X1 through Xm+1 are covalently coupled porphyrinic macrocycles. Light harvesting arrays and solar cells containing such light harvesting rods are also described, along with intermediates useful in such methods and rods produced by such methods.
Claims60
A light harvesting array, comprising:
- (a) a first substrate comprising a first electrode;
- and
- (b) a layer of light harvesting rods electrically coupled to said first electrode, said light harvesting rods in said layer consisting essentially of an oligomer of Formula I:
- A1(Ab+1)b (I)
- wherein:
- (i) b is at least 1;
- (ii) A1 through Ab+1 are covalently coupled rod segments, which segments are different and which segments have sequentially less positive electrochemical potentials;
- and
- (iii) each segment A1 through A1+b comprises a compound of Formula II:
- X1(Xm+1)m (II)
- and wherein:
- m is at least 1;
- and X1 through Xm+1 are covalently coupled porphyrinic macrocycles.
A composition of light harvesting rods, said light harvesting rods in said composition consisting essentially of an oligomer of Formula I:
- A1(Ab+1)b (I)
- wherein:
- (i) b is at least 1;
- (ii) A1 through Ab+1 are covalently coupled rod segments, which segments are different and which segments have sequentially less positive electrochemical potentials;
- and
- (iii) each segment A1 through A1+b comprises a compound of Formula II:
- X1(Xm+1)m (II)
- and wherein:
- m is at least 1;
- and
- X1 through Xm+1 are covalently coupled porphyrinic macrocycles.
A method of making a composition of light harvesting rods, said light harvesting rods comprising an oligomer of Formula I:
- A1(Ab+1)b (I)
- wherein:
- (i) b is at least 1;
- (ii) A1 through Ab+1 are covalently coupled rod segments, which segments are different and which segments have sequentially less positive electrochemical potentials;
- and
- (iii) each segment A1 through A1+b comprises a compound of Formula II:
- X1(Xm+1)m (II)
- and wherein:
- m is at least 1;
- and
- X1 through Xm+1 are covalently coupled porphyrinic macrocycles;
- said method comprising the steps of:
- (a) providing a first rod segment of Formula III and a second rod segment of Formula IV:
- E[X1(Xm+1)m]1f (III)
- G[X1(Xm+1)m]2T (IV)
- wherein:
- E is an end group;
- one of f or G is an ethynyl group;
- the other of f or G is a halo group;
- and
- T is an end group;
- and then
- (b) coupling said segment of Formula III to said segment of Formula IV to produce a compound of Formula I.
A rod segment useful for the production of light harvesting rods, said rod segment comprising a compound of Formula III:
- E[X1(Xm+1)m]1f (III)
- wherein:
- E is selected from the group consisting of bromo, chloro, and fluoro;
- f is a protected or unprotected ethynyl group;
- m is at least 1;
- X1 through Xm+1 are covalently coupled porphyrinic macrocycles;
- and
- each porphyrinic macrocycle X1 through Xm+1 is the same.
Dependencies are inferred from the claim text.