Donor-acceptor-substituted phenylacetylene macrocycles with threefold symmetry

• Verfasst von: Traber, Boris [VerfasserIn]
• Verfasst von: Oeser, Thomas [VerfasserIn]
• Verfasst von: Gleiter, Rolf [VerfasserIn]
• Titel: Donor-acceptor-substituted phenylacetylene macrocycles with threefold symmetry
• Gefeierte Person: Effenberger, Franz [GefeierteR]
• Verf.angabe: Boris Traber, Thomas Oeser, and Rolf Gleiter
• E-Jahr: 2005
• Jahr: 04 April 2005
• Umfang: 10 S.
• Teil: year:2005
• Teil: number:7
• Teil: pages:1283-1292
• Teil: extent:10
• Fussnoten: Dedicated to Professor Franz Effenberger on the occasion of his 75th birthday ; Gesehen am 22.10.2020
• Titel Quelle: Enthalten in: European journal of organic chemistry
• Ort Quelle: Weinheim : Wiley-VCH Verl., 1998
• Jahr Quelle: 2005
• Band/Heft Quelle: (2005), 7, Seite 1283-1292
• ISSN Quelle: 1099-0690
• DOI: doi:10.1002/ejoc.200400603
• Datenträger: Online-Ressource
• Dokumenttyp: Festschrift
• Sprache: eng
• Sach-SW: Alkynes
• Sach-SW: Cyclophanes
• Sach-SW: Donor-acceptor systems
• Sach-SW: Macrocycles
• Sach-SW: UV/Vis spectroscopy
• K10plus-PPN: 1736597663

Abstract

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.