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.
| Author details: | Stefan K. Maier, Georgiy Poluektov, Stefan-S. Jester, Heiko Michael MöllerORCiDGND, Sigurd Hoeger |
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| DOI: | https://doi.org/10.1002/chem.201503211 |
| ISSN: | 0947-6539 |
| ISSN: | 1521-3765 |
| Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/26669967 |
| Title of parent work (English): | Chemistry - a European journal |
| Publisher: | Wiley-VCH |
| Place of publishing: | Weinheim |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2016 |
| Publication year: | 2016 |
| Release date: | 2020/03/22 |
| Tag: | cyclooligomers; scanning tunneling microscopy; self-assembled monolayers; shape-persistent macrocycles; thiophenes |
| Volume: | 22 |
| Number of pages: | 6 |
| First page: | 1379 |
| Last Page: | 1384 |
| Funding institution: | DFG [SFB 813] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
