Synthesis and applications of Rhodamine derivatives as fluorescent probes Mariana Beija, Carlos A. M. Afonso and Jose´ M. G. Martinho Received 26th January 2009 First published as an Advance Article on the web 27th April 2009 DOI: 10.1039/b901612k Rhodamine dyes are widely used as fluorescent probes owing to their high absorption coefficient and broad fluorescence in the visible region of electromagnetic spectrum, high fluorescence quantum yield and photostability. A great interest in the development of new synthetic procedures for preparation of Rhodamine derivatives has arisen in recent years because for most applications the probe must be covalently linked to another (bio)molecule or surface. In this critical review the strategies for modification of Rhodamine dyes and a discussion on the variety of applications of these new derivatives as fluorescent probes are given (108 references). Introduction Rhodamine dyes are fluorophores that belong to the family of xanthenes along with fluorescein and eosin dyes. The general structures of xanthene chromophore and rhodamine dyes are represented in Fig. 1. Due to their excellent photostability and photophysical properties, rhodamines are used as laser dyes, 1,2 fluorescence standards (for quantum yield 3 and polarization 4 ), pigments and as fluorescent probes to characterize the surface of polymer nanoparticles, 5,6 fluidity of lipid membranes, 7 as well as in the detection of polymer-bioconjugates, 8 studies of adsorption of oligonucleotides on latexes, 9,10 studies of structure and dynamics of micelles, 11 single-molecule imaging 12,13 and imaging in living cells. 14–16 Rhodamine derivatives have also been employed as molecular switches, 17 as a thermometer, 18,19 for surface modification of a virus 20 and particularly as chemosensors used either in vitro as in vivo in detection of Hg(II), Cu(II), Fe(III), Cr(III), thiols among other analytes. 21–32 Recently, Gonc¸alves reviewed the fluorescent labelling of biomolecules using organic probes, highlighting the importance of rhodamine derivatives for that application. 33 Fig. 1 Molecular structures of xanthene (A) and rhodamine dyes (B). Centro de Quı´mica-Fı´sica Molecular and IN–Institute of Nanoscience and Nanotechnology, Instituto Superior Te ´cnico, 1049-001, Lisboa, Portugal. E-mail: [email protected], [email protected], [email protected]; Fax: +351 218 464 455 Mariana Beija Mariana Beija was born in Sa ˜o Paulo (Brazil) in 1981. She studied Chemistry in Instituto Superior Te ´cnico (Technical University of Lisbon, Portugal), where she received a school merit award in 2000. In 2004, she started her PhD in Chemistry jointly supervised by Prof. Jose´ M. G. Martinho, in Centro de Quı´mica-Fı´sica Molecular (Instituto Superior Te ´cnico, Lisbon, Portugal), and Dr Marie-The´re`se Charreyre, in Unite ´ Mixte CNRS- bioMe´rieux (Lyon, France). Her doctoral research consisted of the synthesis of novel dye-labelled thermoresponsive block copolymers by RAFT polymerization, involving the synthesis of rhodamine-derived RAFT agents. Carlos A. M. Afonso Carlos A. M. Afonso gradu- ated from University of Coimbra (1984) and received his PhD in 1990 from New University of Lisbon. He worked for one year as post- doctoral fellow at the Imperial College of Science Technology and Medicine under the supervision of Prof. W. B. Motherwell (1990) and one more academic year of sabbatical leave (1997/98) at the University of Bath, UK (Prof. J. Williams) and at the University of Toronto (Professor R. Batey). In 2004 he moved to Instituto Superior Te´cnico as associate professor and in 2008 received his Agregac ¸a ˜o. His research focus is mainly on the development of more sustainable methodologies in asymmetric organic transformations. 2410 | Chem. Soc. Rev., 2009, 38, 2410–2433 This journal is c The Royal Society of Chemistry 2009 CRITICAL REVIEW www.rsc.org/csr | Chemical Society Reviews Downloaded by Universidade Tecnica de Lisboa (UTL) on 03 October 2012 Published on 27 April 2009 on http://pubs.rsc.org | doi:10.1039/B901612K View Online / Journal Homepage / Table of Contents for this issue
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Synthesis and applications of Rhodamine derivatives
as fluorescent probes
Mariana Beija, Carlos A. M. Afonso and Jose M. G. Martinho
Received 26th January 2009
First published as an Advance Article on the web 27th April 2009
DOI: 10.1039/b901612k
Rhodamine dyes are widely used as fluorescent probes owing to their high absorption coefficient
and broad fluorescence in the visible region of electromagnetic spectrum, high fluorescence
quantum yield and photostability. A great interest in the development of new synthetic
procedures for preparation of Rhodamine derivatives has arisen in recent years because for most
applications the probe must be covalently linked to another (bio)molecule or surface. In this
critical review the strategies for modification of Rhodamine dyes and a discussion on the variety
of applications of these new derivatives as fluorescent probes are given (108 references).
Introduction
Rhodamine dyes are fluorophores that belong to the family of
xanthenes along with fluorescein and eosin dyes. The general
structures of xanthene chromophore and rhodamine dyes are
represented in Fig. 1.
Due to their excellent photostability and photophysical
properties, rhodamines are used as laser dyes,1,2 fluorescence
standards (for quantum yield3 and polarization4), pigments
and as fluorescent probes to characterize the surface of
polymer nanoparticles,5,6 fluidity of lipid membranes,7 as well
as in the detection of polymer-bioconjugates,8 studies of
adsorption of oligonucleotides on latexes,9,10 studies of structure
and dynamics of micelles,11 single-molecule imaging12,13 and
imaging in living cells.14–16
Rhodamine derivatives have also been employed as
molecular switches,17 as a thermometer,18,19 for surface
modification of a virus20 and particularly as chemosensors
used either in vitro as in vivo in detection of Hg(II), Cu(II),
Fe(III), Cr(III), thiols among other analytes.21–32 Recently,
Goncalves reviewed the fluorescent labelling of biomolecules
using organic probes, highlighting the importance of
rhodamine derivatives for that application.33
Fig. 1 Molecular structures of xanthene (A) and rhodamine dyes (B).
Centro de Quımica-Fısica Molecular and IN–Institute of Nanoscienceand Nanotechnology, Instituto Superior Tecnico, 1049-001, Lisboa,Portugal. E-mail: [email protected], [email protected],[email protected]; Fax: +351 218 464 455
Mariana Beija
Mariana Beija was born inSao Paulo (Brazil) in 1981.She studied Chemistry inInstituto Superior Tecnico(Technical University ofLisbon, Portugal), where shereceived a school merit awardin 2000. In 2004, she startedher PhD in Chemistry jointlysupervised by Prof. Jose M. G.Martinho, in Centro deQuımica-Fısica Molecular(Instituto Superior Tecnico,Lisbon, Portugal), andDr Marie-Therese Charreyre,in Unite Mixte CNRS-
bioMerieux (Lyon, France). Her doctoral research consistedof the synthesis of novel dye-labelled thermoresponsive blockcopolymers by RAFT polymerization, involving the synthesis ofrhodamine-derived RAFT agents.
Carlos A. M. Afonso
Carlos A. M. Afonso gradu-ated from University ofCoimbra (1984) and receivedhis PhD in 1990 from NewUniversity of Lisbon. Heworked for one year as post-doctoral fellow at the ImperialCollege of Science Technologyand Medicine under thesupervision of Prof. W. B.Motherwell (1990) and onemore academic year ofsabbatical leave (1997/98) atthe University of Bath, UK(Prof. J. Williams) and atthe University of Toronto
(Professor R. Batey). In 2004 he moved to Instituto SuperiorTecnico as associate professor and in 2008 received his Agregacao.His research focus is mainly on the development of moresustainable methodologies in asymmetric organic transformations.
2410 | Chem. Soc. Rev., 2009, 38, 2410–2433 This journal is �c The Royal Society of Chemistry 2009
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state characterized by an electron transfer from the amino
groups to the xanthene ring followed by a rotation between
them.37 The energy of the TICT state is higher than the energy
of the first excited singlet state for the dyes without activated
processes and lower for those with activated internal
conversion. Then, the activated energy dissipation is explained
by the population of the TICT state that is non-emissive and
deactivates quickly to the ground state.38 The non-activated
process involves energy dissipation by C–H and N–H
streching modes coupled with high frequency vibration modes
of the solvent. The N–H vibration modes are found to be very
effective in the dissipation of the electronic energy to hydroxylic
solvents.1,2 Rhodamine 101 (Rho 101) and Rhodamine B
(Rho B) are among the most used rhodamines and present
an interesting behaviour with pH and solvent polarity (Fig. 2).
In acidic solutions, the carboxyl group is protonated and the
rhodamine dye is found in its cationic form. However, in basic
solution, dissociation occurs and the rhodamine dye is
converted into a zwitterion. Although both the cationic and
zwitterionic forms share the same chromophore, the negative
charge has an inductive effect on the central carbon atom of
xanthene chromophore, leading to a hypsochromic shift
of both absorption and fluorescence maxima and a slight
reduction of the extinction coefficient at lmaxabs . The differences
in the specific dye-solvent interaction were also invoked to
explain the small differences in quantum yield and lifetime for
the cationic and zwitterionic forms.39 In less polar organic
solvents, the zwitterionic dye undergoes a reversible
conversion to a colorless lactone due to the interruption of
p–conjugation of the chromophore. Consequently, absorption
of lactones of rhodamine occurs in the UV spectral region and
the fluorescence quantum yield and lifetime are very low.1,40,41
Table 1 summarizes known photophysical parameters of all
forms of Rho 101 and Rho B. The very low quantum yield and
Fig. 2 Molecular structures of three forms of Rho 101 and Rho B in
equilibrium.
Jose M. G. Martinho
J. M. G. Martinho, born inPortugal, in 1950, receivedhis PhD in ChemicalEngineering from InstitutoSuperior Tecnico (TechnicalUniversity of Lisbon, Portugal)in 1982. In 1985, he joinedProf. M. A. Winnik’s researchgroup as a postdoctoral fellowand in 1993 he was invitedProfessor at the OntarioCenter of Materials Researchof the University of Toronto.He is Full Professor ofChemistry and head of theresearch unit, Centro de
Quımica-Fısica Molecular, at IST (Lisbon). His major researchinterests are in the areas of polymers and colloids, photo-chemistry and photophysics and fast chemical kinetics.
This journal is �c The Royal Society of Chemistry 2009 Chem. Soc. Rev., 2009, 38, 2410–2433 | 2411
Conversely, modification of amino groups of xanthene ring
and the preparation of spirolactam derivatives have met an
enormous progress. Derivatization of Rho 110 may be
considered as a very robust method for preparation of
pro-fluorophores. Analogously, reaction of Rho B and Rho
6G with primary amines either by reflux in ethanol or by
formation of acyl chloride with POCl3 can at present be
considered as a standard method for the preparation of metal
chemosensors. Nonetheless, these methods have not been
applied for the synthesis of Rho 101 derivatives. This rigidised
rhodamine derivative has a fluorescence quantum yield of near
one and its photophysical properties are insensitive to the
environment, which could be very interesting for some
applications.
In conclusion, due to these late developments on the
synthetic methods for derivatization of rhodamine dyes it is
today possible to envisage attaching this dye to almost every
molecule of interest, taking advantage of their outstanding
photophysical properties.
Acknowledgements
The authors thank Fundacao para a Ciencia e Tecnologia
(POCI 2010) and FEDER (POCI/QUI/61045/2004) for
financial support. Mariana Beija thanks FCT for a PhD grant
SFRH/BD/18562/2004.
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