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Comparative study of azobenzene and stilbene bridged crown ether p-tert-butylcalix 4 arene

Comparative study of azobenzene and stilbene bridged crown ether p-tert-butylcalix 4 arene
Comparative study of azobenzene and stilbene bridged crown ether p-tert-butylcalix 4 arene
Photo-switchable calixarenes consisting of a stilbene or azobenzene bridge, spanning the narrow rim as a switching unit, were synthesized through reductive coupling of o-, m- and p-bis-benzaldehyde and bis-nitrobenzene-substituted calix[4]arenes. Both cis- and trans-stilbenes were produced from the reductive coupling of the o- and m-bis-benzaldehyde with the cis isomer being predominant for both regioisomers, whilst the coupling of p-bis-benzaldehyde gave only cis product. On the other hand, the only isolable product obtained from the reductive coupling of bis-o- and bis-m-nitrobenzene was the corresponding trans-azobenzene and the coupling product from bis-p-nitrobenzene was not stable. Each of the synthesized compounds showed a photostationary state in their cis-trans isomerization. The complexation of alkali metal ions was observed for only the o-azobenzene derivative suggesting that the lone pair of N-atom in the azo bridge participates in this process.
calixarene, diazobenzene, stilbene, ionophorecrystal-structure, k+ ions, isomerization, complexation, photocontrol, valinomycin, receptors, switches, binding, cone
0040-4020
1317-1324
Rojanathanes, Rojrit
ad698ed2-4f75-4d57-a538-4ca7d356bb1a
Pipoosananakaton, Bongkot
7ced55c3-0dd5-4220-8a04-9af43b383fc1
Tuntulani, Thawatchai
216619a2-97f5-4c47-abc8-fd3dd418c10b
Bhanthumnavin, Worawan
4554c951-b0dd-4ce4-a9f1-ff30aeb7ce0e
Orton, James B.
4e2a471f-9e11-4cb4-abb6-d0398047939f
Cole, Simon J.
e7056a4d-e669-409e-9ca6-7b09aca89286
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Grossel, Martin C.
ec6dc995-8f05-4008-bd93-79c63aab35da
Sukwattanasinitt, Mongkol
2c489552-5f5f-4cef-9c5e-d0366d3c29e7
Rojanathanes, Rojrit
ad698ed2-4f75-4d57-a538-4ca7d356bb1a
Pipoosananakaton, Bongkot
7ced55c3-0dd5-4220-8a04-9af43b383fc1
Tuntulani, Thawatchai
216619a2-97f5-4c47-abc8-fd3dd418c10b
Bhanthumnavin, Worawan
4554c951-b0dd-4ce4-a9f1-ff30aeb7ce0e
Orton, James B.
4e2a471f-9e11-4cb4-abb6-d0398047939f
Cole, Simon J.
e7056a4d-e669-409e-9ca6-7b09aca89286
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Grossel, Martin C.
ec6dc995-8f05-4008-bd93-79c63aab35da
Sukwattanasinitt, Mongkol
2c489552-5f5f-4cef-9c5e-d0366d3c29e7

Rojanathanes, Rojrit, Pipoosananakaton, Bongkot, Tuntulani, Thawatchai, Bhanthumnavin, Worawan, Orton, James B., Cole, Simon J., Hursthouse, Michael B., Grossel, Martin C. and Sukwattanasinitt, Mongkol (2005) Comparative study of azobenzene and stilbene bridged crown ether p-tert-butylcalix 4 arene. Tetrahedron, 61 (5), 1317-1324. (doi:10.1016/j.tet.2004.11.020).

Record type: Article

Abstract

Photo-switchable calixarenes consisting of a stilbene or azobenzene bridge, spanning the narrow rim as a switching unit, were synthesized through reductive coupling of o-, m- and p-bis-benzaldehyde and bis-nitrobenzene-substituted calix[4]arenes. Both cis- and trans-stilbenes were produced from the reductive coupling of the o- and m-bis-benzaldehyde with the cis isomer being predominant for both regioisomers, whilst the coupling of p-bis-benzaldehyde gave only cis product. On the other hand, the only isolable product obtained from the reductive coupling of bis-o- and bis-m-nitrobenzene was the corresponding trans-azobenzene and the coupling product from bis-p-nitrobenzene was not stable. Each of the synthesized compounds showed a photostationary state in their cis-trans isomerization. The complexation of alkali metal ions was observed for only the o-azobenzene derivative suggesting that the lone pair of N-atom in the azo bridge participates in this process.

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More information

Published date: 31 January 2005
Keywords: calixarene, diazobenzene, stilbene, ionophorecrystal-structure, k+ ions, isomerization, complexation, photocontrol, valinomycin, receptors, switches, binding, cone

Identifiers

Local EPrints ID: 20897
URI: http://eprints.soton.ac.uk/id/eprint/20897
ISSN: 0040-4020
PURE UUID: dcc8f3a3-3231-4e79-a486-021c9f80b2d3

Catalogue record

Date deposited: 02 Mar 2006
Last modified: 15 Jul 2019 19:25

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