Donor-acceptor-substituted phenylacetylene macrocycles with threefold symmetry
A stepwise synthesis of the donor-acceptor-substituted macrocycle 5,21,37-tris(diethylamino)-13,29,45-trinitro[2.2.2.2.2.2]metacyclophane-1,9,17,25,33,42-hexayne (1a) from 3,5-bis(3-iodo-5-nitrophenylethynyl)-N,N-diethylaniline (11) and 3,5-bis([3-diethylamino-5-ethynylphenyl]ethynyl)nitrobenzene (1...
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| Main Authors: | , , |
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| Format: | Article (Journal) Festschrift |
| Language: | English |
| Published: |
04 April 2005
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| In: |
European journal of organic chemistry
Year: 2005, Issue: 7, Pages: 1283-1292 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.200400603 |
| Subjects: | |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/ejoc.200400603 Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.200400603 
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| Author Notes: | Boris Traber, Thomas Oeser, and Rolf Gleiter |
| Summary: | A stepwise synthesis of the donor-acceptor-substituted macrocycle 5,21,37-tris(diethylamino)-13,29,45-trinitro[2.2.2.2.2.2]metacyclophane-1,9,17,25,33,42-hexayne (1a) from 3,5-bis(3-iodo-5-nitrophenylethynyl)-N,N-diethylaniline (11) and 3,5-bis([3-diethylamino-5-ethynylphenyl]ethynyl)nitrobenzene (12) failed, mostly due to the low solubility of 1a. The synthesis of the 5,21,37-tris(N,N-di-n-hexylamino) congener of 1a, 1b, was achieved in a one-pot reaction from 1,3-diiodo-5-nitrobenzene (3) and 3,5-diethynyl-N,N-di(n-hexyl)aniline (16) in 23?% yield. X-ray investigations on 1b revealed a planar π ring system with an inner diameter of 10 Å. Despite a high absorbance of 1b at 300 nm, no measurable NLO activity was found. |
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| Item Description: | Dedicated to Professor Franz Effenberger on the occasion of his 75th birthday Gesehen am 22.10.2020 |
| Physical Description: | Online Resource |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.200400603 |