Fast Oxidative Cyclooligomerization towards Low- and High-Symmetry Thiophene Macrocycles
- Macrocycles with quaterthiophene subunits were obtained by cyclooligomerization by direct oxidative coupling of unsubstituted dithiophene moieties. The rings were closed with high selectivity by an α,β′-connection of the thiophenes as proven by NMR spectroscopy. The reaction of the precursor with terthiophene moieties yielded the symmetric α,α′-linked macrocycle in low yield together with various differently connected isomers. Blocking of the β-position of the half-rings yielded selectively the α,α′-linked macrocycle. Selected cyclothiophenes were investigated by scanning tunneling microscopy, which displayed the formation of highly ordered 2D crystalline monolayers.
| Verfasserangaben: | Stefan K. Maier, Georgiy Poluektov, Stefan-S. Jester, Heiko Michael MöllerORCiDGND, Sigurd Hoeger |
|---|---|
| DOI: | https://doi.org/10.1002/chem.201503211 |
| ISSN: | 0947-6539 |
| ISSN: | 1521-3765 |
| Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/26669967 |
| Titel des übergeordneten Werks (Englisch): | Chemistry - a European journal |
| Verlag: | Wiley-VCH |
| Verlagsort: | Weinheim |
| Publikationstyp: | Wissenschaftlicher Artikel |
| Sprache: | Englisch |
| Jahr der Erstveröffentlichung: | 2016 |
| Erscheinungsjahr: | 2016 |
| Datum der Freischaltung: | 22.03.2020 |
| Freies Schlagwort / Tag: | cyclooligomers; scanning tunneling microscopy; self-assembled monolayers; shape-persistent macrocycles; thiophenes |
| Band: | 22 |
| Seitenanzahl: | 6 |
| Erste Seite: | 1379 |
| Letzte Seite: | 1384 |
| Fördernde Institution: | DFG [SFB 813] |
| Organisationseinheiten: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer Review: | Referiert |
