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Detection and Crystal Structure of Hydrogenated Bipentacene as an Intermediate in Thermally Induced Pentacene Oligomerization

Detection and Crystal Structure of Hydrogenated Bipentacene as an Intermediate in Thermally Induced Pentacene Oligomerization

Craig I Hiley, George F S Whitehead, Marco Zanella, Charlene Delacotte, Troy D Manning, Matthew J Rosseinsky

J Org Chem. 2019 Jul 5;84(13):8481-8486.

PMID: 31244161

Abstract:

6,6',13,13'-Tetrahydro-6,6'-bipentacene (HBP), the intermediate molecule connecting pentacene to previously observed peripentacene and extended pentacene oligomers through the formation of a carbon-carbon bond, is synthesized and crystallographically characterized. Heating pentacene to 300 °C under vacuum for 200 h results in pale golden crystals of HBP and amorphous material containing pentacene oligomers, offering experimental evidence that pentacene preferentially dimerizes at the 6,6'-position. Continued heating of HBP results in co-crystals of 6,13-dihydrogenated pentacene and pentacene and further amorphous pentacene oligomers. The amorphous material consists of layered carbonaceous species with a graphenic nature, as determined by Raman spectroscopy and electron microscopy, and suggests HBP as an intermediate to hydrogenated pentacene species and pentacene oligomers, such as peripentacene, of interest in organic electronics.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP135488	Pentacene		135-48-8	Price

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