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Detection and crystal structure of hydrogenated bipentacene as an intermediate in thermally-induced pentacene oligomerization

DOI: 10.1021/acs.joc.9b00671 DOI Help

Authors: Craig I. Hiley (University of Liverpool) , George F. S. Whitehead (University of Liverpool) , Marco Zanella (University of Liverpool) , Charlene Delacotte (University of Liverpool) , Troy D. Manning (University of Liverpool) , Matthew J. Rosseinsky (University of Liverpool)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: The Journal Of Organic Chemistry

State: Published (Approved)
Published: June 2019

Open Access Open Access

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 synthesised and crystallographically characterised. Heating pentacene to 300 ºC under vacuum for 200 hours results in pale golden crystals of HBP and amorphous material containing pentacene oligomers, offering experimental evidence that pentacene preferentially dimerises at the 6,6′- position. Continued heating of HBP results in co-crystals of 6,13-dihydrogenated pentacene (HP) 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.

Subject Areas: Chemistry

Instruments: I11-High Resolution Powder Diffraction

Added On: 10/06/2019 10:58


Discipline Tags:

Chemistry Organic Chemistry

Technical Tags:

Diffraction X-ray Powder Diffraction