Five new metalloporphyrins, $\rm \lbrack Al\sp{III} (TPPCM)Cl\rbrack,$ $\rm \lbrack Al\sp{III} (TPPCN)Cl\rbrack,$ $\rm \lbrack Al\sp{III} (TPPC)Cl\rbrack,$ $\rm \lbrack Cr\sp{III} (TPPCM)Cl\rbrack,$ and $\rm \lbrack Cr\sp{III} (TPPCN)Cl\rbrack,$ have been synthesized and characterized as a first step toward the bulk synthesis of water-soluble C$\sb{60}\sp{.-}$ salts. According to a literature report, Cr$\rm \sp{II}$(TPP) and (Al$\rm \sp{III}$(TPP)$\sp{.-}\rbrack$ (TPP$\sp{2{-}}$ = tetraphenylporphyrinato) reduce C$\sb{60}$ to C$\sb{60}\sp{.-}$ under proper solvent conditions to form an insoluble $\rm \lbrack Cr\sp{III}(TPP)\rbrack\sp+(C\sb{60}\sp{.-})$ or (Al$\rm \sp{III}$(TPP)$\rbrack\sp+$(C$\sb{60}\sp{.-})$ salt. Here it is proposed to derivatize these Cr$\rm \sp{II}$ and Al$\rm \sp{III}$ tetraphenylporphyrins with substituents on the phenyl rings to produce water-soluble $\rm \lbrack Cr\sp{III} (TPPR)\rbrack\sp+(C\sb{60}\sp{.-})$ and $\rm \lbrack Al\sp{III} (TPPR)\rbrack\sp+(C\sb{60}\sp{.-})$ salts. Initial electrochemical data for precursor $\rm \lbrack Al\sp{III} (TPPCM)Cl\rbrack,$ $\rm \lbrack Al\sp{III} (TPPCN)Cl\rbrack,$ $\rm \lbrack Al\sp{III} (TPPC)Cl\rbrack,$ $\rm \lbrack Cr\sp{III} (TPPCM)Cl\rbrack,$ and $\rm \lbrack Cr\sp{III} (TPPCN)Cl\rbrack$ compounds suggest that adding water-solubilizing substituents does not interfere with the electron transfer between the reduced Al$\rm \sp{III}$ and C$\rm \sp{II}$ metalloporphyrins and C$\sb{60}.$ Hence, there is potential to produce bulk amounts of water-soluble C$\sb{60}\sp{.-}$ by this method. The radical anion has 150 A$\sp2$ of paramagnetic surface area (S = 1/2), and possible utility as a new magnetic resonance imaging contrast agent.
| Identifer | oai:union.ndltd.org:RICE/oai:scholarship.rice.edu:1911/14047 |
| Date | January 1996 |
| Creators | DeGroff Puhek, Cynthia Lucil |
| Contributors | Wilson, Lon J. |
| Source Sets | Rice University |
| Language | English |
| Detected Language | English |
| Type | Thesis, Text |
| Format | 90 p., application/pdf |
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