Spectroscopic and photochemical properties of some annulated boldine derivatives

The aim of this study was to determine the influence of the substituent groups on the photostability of eight boldine derivatives, including some oxazole and oxazinone derivatives, in order to increase the sunscreen protection properties previously demonstrated for boldine. Such derivatives showed bands similar to those of boldine in the absorption and emission spectrum. The spectroscopic properties are pH dependent. The photostability of the derivative compounds was higher than that of boldine, in accordance with the low value of the photoconsumption quantum yield determined. The low fluorescence quantum yield values observed for boldine 1 and 4 as both base and hydrochloride derivative compounds led us to postulate that these compounds are deactivated by a mechanism different to the fluorescence pathway, probably due to the electron-withdrawing inductive effect of NO for boldine 1, and to the increase of the aromatic framework for boldine 4.

Saved in:
Bibliographic Details
Main Authors: Hidalgo,María E, Alarcón,Myriam G., Ojeda,Juan R., Fernández,Ernesto C., Sobarzo-Sánchez,Eduardo M., De la Fuent,Julio R.
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2010
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001200006
Tags: Add Tag
No Tags, Be the first to tag this record!
id oai:scielo:S0103-50532010001200006
record_format ojs
spelling oai:scielo:S0103-505320100012000062010-12-16Spectroscopic and photochemical properties of some annulated boldine derivativesHidalgo,María EAlarcón,Myriam G.Ojeda,Juan R.Fernández,Ernesto C.Sobarzo-Sánchez,Eduardo M.De la Fuent,Julio R. boldine oxazol-oxazinone derivatives photostability The aim of this study was to determine the influence of the substituent groups on the photostability of eight boldine derivatives, including some oxazole and oxazinone derivatives, in order to increase the sunscreen protection properties previously demonstrated for boldine. Such derivatives showed bands similar to those of boldine in the absorption and emission spectrum. The spectroscopic properties are pH dependent. The photostability of the derivative compounds was higher than that of boldine, in accordance with the low value of the photoconsumption quantum yield determined. The low fluorescence quantum yield values observed for boldine 1 and 4 as both base and hydrochloride derivative compounds led us to postulate that these compounds are deactivated by a mechanism different to the fluorescence pathway, probably due to the electron-withdrawing inductive effect of NO for boldine 1, and to the increase of the aromatic framework for boldine 4.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.21 n.12 20102010-12-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001200006en10.1590/S0103-50532010001200006
institution SCIELO
collection OJS
country Brasil
countrycode BR
component Revista
access En linea
databasecode rev-scielo-br
tag revista
region America del Sur
libraryname SciELO
language English
format Digital
author Hidalgo,María E
Alarcón,Myriam G.
Ojeda,Juan R.
Fernández,Ernesto C.
Sobarzo-Sánchez,Eduardo M.
De la Fuent,Julio R.
spellingShingle Hidalgo,María E
Alarcón,Myriam G.
Ojeda,Juan R.
Fernández,Ernesto C.
Sobarzo-Sánchez,Eduardo M.
De la Fuent,Julio R.
Spectroscopic and photochemical properties of some annulated boldine derivatives
author_facet Hidalgo,María E
Alarcón,Myriam G.
Ojeda,Juan R.
Fernández,Ernesto C.
Sobarzo-Sánchez,Eduardo M.
De la Fuent,Julio R.
author_sort Hidalgo,María E
title Spectroscopic and photochemical properties of some annulated boldine derivatives
title_short Spectroscopic and photochemical properties of some annulated boldine derivatives
title_full Spectroscopic and photochemical properties of some annulated boldine derivatives
title_fullStr Spectroscopic and photochemical properties of some annulated boldine derivatives
title_full_unstemmed Spectroscopic and photochemical properties of some annulated boldine derivatives
title_sort spectroscopic and photochemical properties of some annulated boldine derivatives
description The aim of this study was to determine the influence of the substituent groups on the photostability of eight boldine derivatives, including some oxazole and oxazinone derivatives, in order to increase the sunscreen protection properties previously demonstrated for boldine. Such derivatives showed bands similar to those of boldine in the absorption and emission spectrum. The spectroscopic properties are pH dependent. The photostability of the derivative compounds was higher than that of boldine, in accordance with the low value of the photoconsumption quantum yield determined. The low fluorescence quantum yield values observed for boldine 1 and 4 as both base and hydrochloride derivative compounds led us to postulate that these compounds are deactivated by a mechanism different to the fluorescence pathway, probably due to the electron-withdrawing inductive effect of NO for boldine 1, and to the increase of the aromatic framework for boldine 4.
publisher Sociedade Brasileira de Química
publishDate 2010
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001200006
work_keys_str_mv AT hidalgomariae spectroscopicandphotochemicalpropertiesofsomeannulatedboldinederivatives
AT alarconmyriamg spectroscopicandphotochemicalpropertiesofsomeannulatedboldinederivatives
AT ojedajuanr spectroscopicandphotochemicalpropertiesofsomeannulatedboldinederivatives
AT fernandezernestoc spectroscopicandphotochemicalpropertiesofsomeannulatedboldinederivatives
AT sobarzosanchezeduardom spectroscopicandphotochemicalpropertiesofsomeannulatedboldinederivatives
AT delafuentjulior spectroscopicandphotochemicalpropertiesofsomeannulatedboldinederivatives
_version_ 1756403415075782656