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...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Hauptverfasser: Traber, Boris (VerfasserIn) , Oeser, Thomas (VerfasserIn) , Gleiter, Rolf (VerfasserIn)
Dokumenttyp: Article (Journal) Festschrift
Sprache:Englisch
Veröffentlicht: 04 April 2005
In: European journal of organic chemistry
Year: 2005, Heft: 7, Pages: 1283-1292
ISSN:1099-0690
DOI:10.1002/ejoc.200400603
Schlagworte:
Online-Zugang: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
Volltext
Verfasserangaben:Boris Traber, Thomas Oeser, and Rolf Gleiter

MARC

LEADER 00000caa a2200000 c 4500
001 1736597663
003 DE-627
005 20220819001335.0
007 cr uuu---uuuuu
008 201026s2005 xx |||||o 00| ||eng c
024 7 |a 10.1002/ejoc.200400603  |2 doi 
035 |a (DE-627)1736597663 
035 |a (DE-599)KXP1736597663 
035 |a (OCoLC)1341373244 
040 |a DE-627  |b ger  |c DE-627  |e rda 
041 |a eng 
084 |a 30  |2 sdnb 
100 1 |a Traber, Boris  |e VerfasserIn  |0 (DE-588)1220053872  |0 (DE-627)1736243292  |4 aut 
245 1 0 |a Donor-acceptor-substituted phenylacetylene macrocycles with threefold symmetry  |c Boris Traber, Thomas Oeser, and Rolf Gleiter 
264 1 |c 04 April 2005 
300 |a 10 
336 |a Text  |b txt  |2 rdacontent 
337 |a Computermedien  |b c  |2 rdamedia 
338 |a Online-Ressource  |b cr  |2 rdacarrier 
500 |a Dedicated to Professor Franz Effenberger on the occasion of his 75th birthday 
500 |a Gesehen am 22.10.2020 
520 |a 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. 
650 4 |a Alkynes 
650 4 |a Cyclophanes 
650 4 |a Donor-acceptor systems 
650 4 |a Macrocycles 
650 4 |a UV/Vis spectroscopy 
655 7 |a Festschrift  |0 (DE-588)4016928-5  |0 (DE-627)104400986  |0 (DE-576)208917802  |2 gnd-content 
700 1 |a Oeser, Thomas  |e VerfasserIn  |0 (DE-588)1025249038  |0 (DE-627)721919715  |0 (DE-576)170725553  |4 aut 
700 1 |a Gleiter, Rolf  |d 1936-  |e VerfasserIn  |0 (DE-588)1035293870  |0 (DE-627)747237077  |0 (DE-576)382908473  |4 aut 
700 1 |a Effenberger, Franz  |d 1930-2024  |e GefeierteR  |0 (DE-588)131763636  |0 (DE-627)51360863X  |0 (DE-576)298726084  |4 hnr 
773 0 8 |i Enthalten in  |t European journal of organic chemistry  |d Weinheim : Wiley-VCH Verl., 1998  |g (2005), 7, Seite 1283-1292  |h Online-Ressource  |w (DE-627)269534539  |w (DE-600)1475010-7  |w (DE-576)07788468X  |x 1099-0690  |7 nnas  |a Donor-acceptor-substituted phenylacetylene macrocycles with threefold symmetry 
773 1 8 |g year:2005  |g number:7  |g pages:1283-1292  |g extent:10  |a Donor-acceptor-substituted phenylacetylene macrocycles with threefold symmetry 
856 4 0 |u https://doi.org/10.1002/ejoc.200400603  |x Verlag  |x Resolving-System  |z lizenzpflichtig  |3 Volltext  |7 1 
856 4 0 |u https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.200400603  |x Verlag  |z lizenzpflichtig  |3 Volltext  |7 1 
951 |a AR 
992 |a 20201026 
993 |a Article 
994 |a 2005 
998 |g 1035293870  |a Gleiter, Rolf  |m 1035293870:Gleiter, Rolf  |d 120000  |e 120000PG1035293870  |k 0/120000/  |p 3  |y j 
998 |g 1025249038  |a Oeser, Thomas  |m 1025249038:Oeser, Thomas  |d 120000  |d 120100  |e 120000PO1025249038  |e 120100PO1025249038  |k 0/120000/  |k 1/120000/120100/  |p 2 
998 |g 1220053872  |a Traber, Boris  |m 1220053872:Traber, Boris  |p 1  |x j 
999 |a KXP-PPN1736597663  |e 3786428476 
BIB |a Y 
SER |a journal 
JSO |a {"physDesc":[{"extent":"10 S."}],"relHost":[{"type":{"bibl":"periodical","media":"Online-Ressource"},"note":["Gesehen am 21.01.04"],"disp":"Donor-acceptor-substituted phenylacetylene macrocycles with threefold symmetryEuropean journal of organic chemistry","recId":"269534539","language":["eng"],"pubHistory":["1998 -"],"part":{"extent":"10","text":"(2005), 7, Seite 1283-1292","pages":"1283-1292","issue":"7","year":"2005"},"title":[{"title_sort":"European journal of organic chemistry","title":"European journal of organic chemistry"}],"physDesc":[{"extent":"Online-Ressource"}],"origin":[{"dateIssuedDisp":"1998-","publisher":"Wiley-VCH Verl.","dateIssuedKey":"1998","publisherPlace":"Weinheim"}],"id":{"doi":["10.1002/(ISSN)1099-0690"],"eki":["269534539"],"zdb":["1475010-7"],"issn":["1099-0690"]}}],"name":{"displayForm":["Boris Traber, Thomas Oeser, and Rolf Gleiter"]},"origin":[{"dateIssuedKey":"2005","dateIssuedDisp":"04 April 2005"}],"id":{"doi":["10.1002/ejoc.200400603"],"eki":["1736597663"]},"type":{"bibl":"article-journal","media":"Online-Ressource"},"note":["Dedicated to Professor Franz Effenberger on the occasion of his 75th birthday","Gesehen am 22.10.2020"],"language":["eng"],"recId":"1736597663","person":[{"display":"Traber, Boris","roleDisplay":"VerfasserIn","role":"aut","family":"Traber","given":"Boris"},{"given":"Thomas","family":"Oeser","role":"aut","display":"Oeser, Thomas","roleDisplay":"VerfasserIn"},{"family":"Gleiter","given":"Rolf","roleDisplay":"VerfasserIn","display":"Gleiter, Rolf","role":"aut"},{"display":"Effenberger, Franz","roleDisplay":"GefeierteR","role":"hnr","family":"Effenberger","given":"Franz"}],"title":[{"title":"Donor-acceptor-substituted phenylacetylene macrocycles with threefold symmetry","title_sort":"Donor-acceptor-substituted phenylacetylene macrocycles with threefold symmetry"}]} 
SRT |a TRABERBORIDONORACCEP0420