Detection and Crystal Structure of Hydrogenated Bipentacene as an Intermediate in Thermally Induced Pentacene Oligomerization
| Autor: | George F. S. Whitehead, Charlene Delacotte, Craig I. Hiley, Matthew J. Rosseinsky, Troy D. Manning, Marco Zanella |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Chemistry Organic Chemistry Crystal structure 010402 general chemistry 7. Clean energy 01 natural sciences Article 0104 chemical sciences Amorphous solid law.invention Pentacene Crystallography symbols.namesake chemistry.chemical_compound law symbols Molecule Electron microscope Raman spectroscopy |
| Zdroj: | The Journal of Organic Chemistry JOURNAL OF ORGANIC CHEMISTRY |
| ISSN: | 1520-6904 |
| Popis: | 6,6′,13,13′- tetrahydro-6,6′-bipentacene (HBP), the first intermediate molecule between pentacene and peripentacene and extended pentacene oligomers, is synthesised and crystallographically characterised for the first time. Heating pentacene to 300 oC under vacuum for 200 hours results in pale golden crystals of HBP and amorphous material containing pentacene oligomers, and is the first 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 shows the importance of HBP as an intermediate to hydrogenated pentacene species and pentacene oligomers. The synthesis of HBP from pentacene could be useful as a starting material in the rational synthesis of peripentacene towards organic electronic devices. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|