Insights into the complexation of N-Allyl-4-(4-(N-phenylureido)benzylamino)-1,8-naphthalimide with various anions

Abstract A new urea functionalised 4-amino-1,8-naphthalimide based fluorescent anion sensor was synthesised in 64% yield over three steps. Fluorescence and 1H NMR titrations showed that the sensor complexes strongly with acetate and dihydrogen phosphate and to a lesser extent bromide. The correspond...

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Autores principales:	Andrew J. Blok, Martin R. Johnston, Claire E. Lenehan
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/294b92eb652440208286879e46bb108b
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spelling	oai:doaj.org-article:294b92eb652440208286879e46bb108b2021-12-02T12:32:44ZInsights into the complexation of N-Allyl-4-(4-(N-phenylureido)benzylamino)-1,8-naphthalimide with various anions10.1038/s41598-017-02470-02045-2322https://doaj.org/article/294b92eb652440208286879e46bb108b2017-05-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-02470-0https://doaj.org/toc/2045-2322Abstract A new urea functionalised 4-amino-1,8-naphthalimide based fluorescent anion sensor was synthesised in 64% yield over three steps. Fluorescence and 1H NMR titrations showed that the sensor complexes strongly with acetate and dihydrogen phosphate and to a lesser extent bromide. The corresponding binding stoichiometries were examined using 1H NMR titrations. Results show that the sensor molecule initially forms 1:1 complexes through hydrogen bonding to the urea moiety, followed by secondary complexation to form higher order host:guest stoichiometries. Specifically, oxyanions complex to the sensor via hydrogen bonding through synergistic aryl C-H and N-H anion interactions in a 1:2 sensor:oxyanion arrangement. Furthermore, 2:1 sensor:oxyanion complexes are formed through an oxyanion linkage between two urea functionalities on different host molecules. This contrasts the majority of previous reports for similar hosts, which indicate 1:1 binding stoichiometry.Andrew J. BlokMartin R. JohnstonClaire E. LenehanNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-7 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Andrew J. Blok Martin R. Johnston Claire E. Lenehan Insights into the complexation of N-Allyl-4-(4-(N-phenylureido)benzylamino)-1,8-naphthalimide with various anions
description	Abstract A new urea functionalised 4-amino-1,8-naphthalimide based fluorescent anion sensor was synthesised in 64% yield over three steps. Fluorescence and 1H NMR titrations showed that the sensor complexes strongly with acetate and dihydrogen phosphate and to a lesser extent bromide. The corresponding binding stoichiometries were examined using 1H NMR titrations. Results show that the sensor molecule initially forms 1:1 complexes through hydrogen bonding to the urea moiety, followed by secondary complexation to form higher order host:guest stoichiometries. Specifically, oxyanions complex to the sensor via hydrogen bonding through synergistic aryl C-H and N-H anion interactions in a 1:2 sensor:oxyanion arrangement. Furthermore, 2:1 sensor:oxyanion complexes are formed through an oxyanion linkage between two urea functionalities on different host molecules. This contrasts the majority of previous reports for similar hosts, which indicate 1:1 binding stoichiometry.
format	article
author	Andrew J. Blok Martin R. Johnston Claire E. Lenehan
author_facet	Andrew J. Blok Martin R. Johnston Claire E. Lenehan
author_sort	Andrew J. Blok
title	Insights into the complexation of N-Allyl-4-(4-(N-phenylureido)benzylamino)-1,8-naphthalimide with various anions
title_short	Insights into the complexation of N-Allyl-4-(4-(N-phenylureido)benzylamino)-1,8-naphthalimide with various anions
title_full	Insights into the complexation of N-Allyl-4-(4-(N-phenylureido)benzylamino)-1,8-naphthalimide with various anions
title_fullStr	Insights into the complexation of N-Allyl-4-(4-(N-phenylureido)benzylamino)-1,8-naphthalimide with various anions
title_full_unstemmed	Insights into the complexation of N-Allyl-4-(4-(N-phenylureido)benzylamino)-1,8-naphthalimide with various anions
title_sort	insights into the complexation of n-allyl-4-(4-(n-phenylureido)benzylamino)-1,8-naphthalimide with various anions
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/294b92eb652440208286879e46bb108b
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Insights into the complexation of N-Allyl-4-(4-(N-phenylureido)benzylamino)-1,8-naphthalimide with various anions

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