Synthesis and Electrochemical Properties of Phthalocyanine–Fullerene Hybrids

Abstract

Phthalocyanines linked to C60 have been synthesized by two general strategies. One of them involves the addition of an azomethine ylide prepared in situ from a formyl phthalocyanine to C60, and the other one involves a statistical condensation of two substituted phthalonitriles, one of them bearing the C60 moiety covalently attached. These new phthalocyanine-fullerene dyads have been studied by cyclic voltammetry and Osteryoung square wave voltammetry, and inter- and intramolecular electronic interactions between the two electroactive subunits have been demonstrated.

An Update on the Synthesis of Benzoxazoles

“…Salome Rodreguez Morgade Gouloumis et al [42] reported the synthesis of benzoxazole derivatives. The aza-Wittig reaction of the triphenyl phosphoranylideneamino-1,4-benzoquinone with aryl isocyanates and aryl chlorides allows the preparation of benzoxazole derivatives (72).…”

Synthetic approaches to asymmetric phthalocyanines and their analogues

“…In particular, as shown in the laboratories of Torres, van Lier, and many others, the mono-iodo A 3 B phthalocyanines 62 can easily be made to undergo a variety of coupling reactions (Scheme 23). 218,220,221,223,227,228,[236][237][238][239][240][241][242] This precursor can be used for the introduction of direct carboncarbon bonds as aryl, alkenyl, and alkynyl substituents. 217,219,220,226,234,235 In addition, the Buchwald reaction can be used for carbon-nitrogen bond formation.…”

“…218,220 Similarly, palladium-catalyzed Stille reaction between monoiodo-substituted A 3 B phthalocyanines 62 and tributylstannylethylene leads to formation of the vinyl-containing phthalocyanine 74 (Scheme 26). 221 In another synthetic strategy, carboxaldehyde-containing asymmetric phthalocyanine could be used for preparation of alkene-substituted phthalocyanines. The aldehydic A 3 B phthalocyanines can be prepared in two steps.…”

“…The protected A 3 B phthalocyanine can then be deprotected to generate the peripheral aldehyde substituent. 221 Another synthetic pathway to prepare aldehyde-containing phthalocyanine 75 is by oxidative cleavage of vinylphthalocyanine (Scheme 26). 221 Prepared by any of the above-mentioned methods, an aldehyde-containing phthalocyanine can then form a desired conjugated alkene-bridged binuclear phthalocyanine in a Wittig reaction.…”

“…221 Another synthetic pathway to prepare aldehyde-containing phthalocyanine 75 is by oxidative cleavage of vinylphthalocyanine (Scheme 26). 221 Prepared by any of the above-mentioned methods, an aldehyde-containing phthalocyanine can then form a desired conjugated alkene-bridged binuclear phthalocyanine in a Wittig reaction. 222 The Heck reaction can also be used to prepare binuclear alkenyl-bridged A 3 B phthalocyanines.…”