NDLI: Spectroscopic Response of Ferrocene Derivatives Bearing a BODIPY Moiety to Water: A New Dissociation Reaction

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Spectroscopic Response of Ferrocene Derivatives Bearing a BODIPY Moiety to Water: A New Dissociation Reaction

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Chen, Suming Chen, Wei Ma, Huimin Shi, Wen
Description	Author Affiliation: Chen S ( Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.)
Abstract	Ferrocence and its derivatives have long been known to be a class of stable organometallic compounds, and their dissociation usually occurs under harsh conditions. Here we report a new type of ferrocene derivatives, 4,4-difluoro-8-ferrocenyl-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene and 4,4-difluoro-2,6-diethyl-8-ferrocenyl-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene, which surprisingly can hydrolyze under mild conditions. These two derivatives, initially developed as donor–acceptor probes for reactive oxygen species by incorporating the electron donor of ferrocene as a quencher into the fluorophore of BODIPY (boron dipyrromethene difluoride), barely emit fluorescence. Upon reaction with $H_{2}O$ under the irradiation of natural light at room temperature, however, both of the probes display a dramatic color change and fluorescence retrievement. Detailed experimental results reveal that the reaction of the probes with $H_{2}O$ leads to the removal of a cyclopentadiene unit and iron(II), yielding a BODIPY derivative that retains the other cyclopentadiene unit and shows a large fluorescence enhancement (over 100-fold). Moreover, the increase in fluorescence intensity is directly proportional to microamount of water, and the presence of both light and $H_{2}O$ is indispensable in the reaction, which makes the present system of great potential not only for determining water but also for forming a AND logic gate. Most importantly, the present mild dissociation reaction may give a new insight into the stability of ferrocene and its derivatives.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	3
Volume Number	18
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2012-01-16
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Boron Compounds Chemical Synthesis Ferrous Compounds Fluorescent Dyes Chemistry Electron Spin Resonance Spectroscopy Molecular Structure Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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