Improved syntheses of high hole mobility phthalocyanines: A case of steric assistance in the cyclo-oligomerisation of phthalonitriles

It has been shown that the base-initiated cyclo-oligomerisation of phthalonitriles is favoured by bulky α-substituents making it possible to obtain the metal-free phthalocyanine directly and in high yield. The phthalocyanine with eight α-isoheptyl substituents gives a high time-of-flight hole mobili...

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Published inBeilstein journal of organic chemistry Vol. 8; no. 1; pp. 120 - 128
Main Authors Tate, Daniel J, Anémian, Rémi, Bushby, Richard J, Nanan, Suwat, Warriner, Stuart L, Whitaker, And Benjamin J
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut 24.01.2012
Subjects
Chemistry
Full Research Paper
high hole mobility
phthalocyanine
steric assistance
Thorpe–Ingold effect
time-of-flight
phthalocyanine
Thorpe–Ingold effect
high hole mobility
steric assistance
time-of-flight
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Summary:It has been shown that the base-initiated cyclo-oligomerisation of phthalonitriles is favoured by bulky α-substituents making it possible to obtain the metal-free phthalocyanine directly and in high yield. The phthalocyanine with eight α-isoheptyl substituents gives a high time-of-flight hole mobility of 0.14 cm(2)·V(-1)·s(-1) within the temperature range of the columnar hexagonal phase, that is 169-189 °C.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.8.14