Synthesis of 20-iodochlorophyll derivatives and their properties including reactivity, electronic absorption, and self-aggregation

Bottom-Up Hierarchical Self-Assembly of Chiral Porphyrins through Coordination and Hydrogen Bonds

“…In all of these systems, a metal ion is coordinated in the core of the chromophore, and this feature plays an important role in their self-assembly and function. To understand the role of metal ions and self-organization of porphyrins, enzymes and light-harvesting systems mimicking the natural pigments have been synthesized and studied, confirming the importance of the supramolecular structure on the light harvesting ability. − …”

“…To understand the role of metal ions and self-organization of porphyrins, enzymes and light-harvesting systems mimicking the natural pigments have been synthesized and studied, confirming the importance of the supramolecular structure on the light harvesting ability. [8][9][10][11][12] Self-assembled chiral systems based on synthetic porphyrins present a broad range of potential applications in areas such as photovoltaic cells, 13 sensors, 14 optoelectronics 15 and nanoelectronic devices 16 and also non-linear optical materials. 17 The number and position of the stereogenic centers in molecules united by covalent or non-covalent bonds directly affect the chiral transfer from the molecular level up to the supramolecular aggregates that they form in solution and consequently their optical activity can be modified.…”

Alternative synthesis of 3-acetyl, 3-epoxy, and 3-formyl chlorins from a 3-vinyl chlorin, methyl pyropheophorbide-a, via iodination

“…[21][22][23][24][25][26][27][28][29][30][31][32][33] We have studied reaction of 1 with I 2 and phenyliodine(III) bis(trifluoroacetate) (PIFA), and established the conditions for selective iodination at the C3-vinyl group and the C20-position, respectively. 34,35 The C3-vinyl group was iodinated by 1 equiv I 2 and 0.5 equiv PIFA to give the iodinated intermediate (possibly the C3-iodonium form), and 2 equiv I 2 together with 1 equiv PIFA enabled additional iodination at the C20-position. The C3-iodonium was transformed into the iodohydrin by treatment of water, while the iodine atom was removed from the iodonium by NaN 3 .…”