Optical Sensors and Switches (Molecular and Supramolecular Photochemistry)

534 Pages·2001·4.51 MB·English

by  V. Ramamurthy

ISBN:0-8247-0571-8
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Preface
During the past decade the field of photochemistry has focused increasingly
on the development of photochemical systems and materials that respond in
a controllable manner to chemical and/or optical stimuli. Photoresponsive sys-
tems and materials are exceedingly useful, as exemplified by the fact that they
formthebasisforavarietyoftechnologicallyimportantprocessesandproducts
such as chemical sensors, photochromic optical elements, optical data storage
media, photoresists, organic light emitting diodes, optical limiters, photocon-
ductorsforuseinxerography,andmolecularsystemsforphotodynamictherapy.
Although many useful photoresponsive systems are based on “simple” molec-
ular photochemistry—for example, photochromic azobenzene and spiropyrans
are used in optical data storage media and ruthenium and platinum complexes
are useful optical oxygen sensors—solutions to many high-technology applica-
tions of current interest inevitably require complex supramolecular assemblies
to achieve the desired photoresponsive function.
The present volume highlights recent work from leading chemical and
materials research scientists that are developing supramolecular photochemical
systems that possess unique functions as optical sensors and/or switches. The
chapters in this volume span the range from fundamental studies of unique and
novel new chemical systems to applications-driven research in which the objec-
tive is to develop new materials having useful properties for high-technology
applications such as detecting biologically relevant target molecules and optical
signal multiplexing.
Chapters 1 through 4 feature work on supramolecular and polymer sys-
tems that function as sensors for a variety of chemical and biological targets. In
Chapter1,RudzinskiandNoceragiveanexcitingoverviewofresearchfocusing
iii
iv Preface
on the development of unique supramolecular sensors that combine an organic
receptor unit (a bucket) with a luminescent reporter moiety. These “buckets of
light” are highly useful in sensing a variety of targets using luminescence as
the method for detection. In Chapter 2, de Silva and his coauthors present an
authoritative overview of supramolecular optical sensors that function by com-
petition between photoluminescence and photoinduced electron transfer. These
luminescent PET sensors have been widely applied by the authors as well as
other groups for ion and pH sensing in chemically and biologically relevant
systems. Andersson and Schmehl, in Chapter 3, provide an introduction to the
application of electrogenerated chemiluminescence (ECL) to chemical sensing.
This chapter introduces the method of ECL sensing and provides several exam-
ples of its application. Chapter 4 describes a very interesting new application
of supramolecular photophysics to sensing chemical and biological analytes.
Whitten and coworkers from QTL Biosystems (QTL = quencher-tether-ligand)
describetheremarkablysensitivefluorescencequenchingofπ-conjugatedpoly-
electrolytesbypositivelychargedspeciessuchasviologens.Theyhaveparlayed
thiseffectintothedesignofsupramolecularsystemsthatcandetectbiologically
relevant analytes at nM concentrations.
Chapters 5 through 8 describe new polymeric materials that display use-
ful optical properties. In Chapter 5, Lees discusses the use of photoluminescent
metalcomplexesasprobestoexplorethepropertiesofpolymerswhileinChap-
ters 6, 7, and 8 Wang, Wiederrecht and Sponslor, respectively, and coauthors
describe the properties of unique new polymer- and liquid crystalline–based
materials. In the final chapters a variety of novel polymeric and supramolecular
materialsthatdisplayinterestingandusefulphotochemicalandopticalproperties
are described.
Nagamura describes in Chapter 9 the fabrication and properties of supra-
molecularandpolymericsystemsthatdisplayuniquelinearandnonlinearoptical
response. Such materials may find application in high-density information pro-
cessing systems of the future. Chapter 10, by Shinkai and James, describes the
properties of supramolecular photoswitchable ion receptors. Finally, in Chap-
ter 11, Ishikawa and Ye discuss the application of state-of-the art fluorescence
methods to explore the properties of polymers with nm-scale resolution.
Taken together, the contributions in this volume provide an overview of
work in the field of photochemistry that is directed toward the development of
state-of-theartsupramolecularsystemsandmaterialsthatdisplayuniqueoptical
response. The book will serve as a valuable resource and guide to scientists
engaged in chemical and materials research as well as to students seeking to
learn more about this exciting field of scientific research.
Kirk S. Schanze
V. Ramamurthy
Contents
Preface iii
Contributors vii
Contents of Previous Volumes ix
1. Buckets of Light 1
Christina M. Rudzinski and Daniel G. Nocera
2. Luminescent PET Signaling Systems 93
A. Prasanna de Silva, David B. Fox, Thomas S. Moody,
and Sheenagh M. Weir
3. Sensors Based on Electrogenerated Chemiluminescence 153
Ann-Margret Andersson and Russell H. Schmehl
4. From Superquenching to Biodetection: Building Sensors
Based on Fluorescent Polyelectrolytes 189
David Whitten, Liaohai Chen, Robert Jones, Troy Bergstedt,
Peter Heeger, and Duncan McBranch
5. Luminescent Metal Complexes as Spectroscopic Probes of
Monomer/Polymer Environments 209
Alistair J. Lees
v
vi Contents
6. Photorefractive Effect in Polymeric and Molecular Materials 257
Liming Wang, Man-Kit Ng, Qing Wang, and Luping Yu
7. Dynamic Holography in Photorefractive Liquid Crystals 319
Gary P. Wiederrecht
8. Hologram Switching and Erasing Strategies With
Liquid Crystals 363
Michael B. Sponsler
9. Novel Molecular Photonics Materials and Devices 387
Toshihiko Nagamura
10. Molecular Recognition Events Controllable by Photochemical
Triggers or Readable by Photochemical Outputs 429
Seiji Shinkai and Tony D. James
11. Probing Nanoenvironments Using Functional Chromophores 457
Mitsuru Ishikawa and Jing Yong Ye
Index 515
Contributors
Ann-Margret Andersson Department of Chemistry, Tulane University, New
Orleans, Louisiana
Troy Bergstedt, Ph.D. QTL Biosystems, LLC, Santa Fe, New Mexico
Liaohai Chen, Ph.D. Los Alamos National Laboratory, Los Alamos, New
Mexico
A. Prasanna de Silva, Ph.D. School of Chemistry, Queen’s University of
Belfast, Belfast, Northern Ireland
David B. Fox School of Chemistry, Queen’s University of Belfast, Belfast,
Northern Ireland
Peter Heeger, M.D. Case Western Reserve University, Cleveland, Ohio
Mitsuru Ishikawa Joint Research Center for Atom Technology (JRCAT) and
Angstrom Technology Partnership (ATP), Ibaraki, Japan
Tony D. James, Ph.D. Department of Chemistry, University of Birmingham,
Birmingham, United Kingdom
Robert Jones, Ph.D. QTL Biosystems, LLC, Santa Fe, New Mexico
Alistair J. Lees, Ph.D. Department of Chemistry, State University of New
York at Binghamton, Binghamton, New York
vii
viii Contributors
Duncan McBranch, Ph.D. QTL Biosystems, LLC, Santa Fe, New Mexico
ThomasS.Moody SchoolofChemistry,Queen’sUniversityofBelfast,Belfast,
Northern Ireland
Toshihiko Nagamura, Ph.D. Molecular Photonics Laboratory, Research In-
stitute of Electronics, Shizuoka University, Hamamatsu, Japan
Man-KitNg,Ph.D. DepartmentofChemistryandTheJamesFranckInstitute,
University of Chicago, Chicago, Illinois
Daniel G. Nocera, Ph.D. Department of Chemistry, Massachusetts Institute
of Technology, Cambridge, Massachusetts
ChristinaM.Rudzinski DepartmentofChemistry,MassachusettsInstituteof
Technology, Cambridge, Massachusetts
RussellH.Schmehl,Ph.D. DepartmentofChemistry,TulaneUniversity,New
Orleans, Louisiana
Seiji Shinkai, Ph.D. Department of Chemistry and Biochemistry, Graduate
School of Engineering, Kyushu University, Fukuoka, Japan
MichaelB.Sponsler,Ph.D. DepartmentofChemistryandW.M.KeckCenter
for Molecular Electronics, Syracuse University, Syracuse, New York
Liming Wang, Ph.D. Department of Chemistry and The James Franck Insti-
tute, University of Chicago, Chicago, Illinois
QingWang,Ph.D. DepartmentofChemistryandTheJamesFranckInstitute,
University of Chicago, Chicago, Illinois
SheenaghM.Weir SchoolofChemistry,Queen’sUniversityofBelfast,Belfast,
Northern Ireland
David Whitten, Ph.D. QTL Biosystems, LLC, Santa Fe, New Mexico
Gary P. Wiederrecht, Ph.D. Chemistry Division, Argonne National Labora-
tory, Argonne, Illinois
Jing Yong Ye Joint Research Center for Atom Technology (JRCAT) and
Angstrom Technology Partnership (ATP), Ibaraki, Japan
Luping Yu, Ph.D. Department of Chemistry and The James Franck Institute,
University of Chicago, Chicago, Illinois
Contents of Previous Volumes
Volume 1. Organic Photochemistry
1. The Photochemistry of Sulfoxides and Related Compounds
William S. Jenks, Daniel D. Gregory, Yushen-Guo, Woojae Lee,
and Troy Tetzlaff
2. The Photochemistry of Pyrazoles and Isothiazoles
James W. Pavlik
3. Photochemistry of (S-Hetero)cyclic Unsaturated Carbonyl Compounds
Paul Margaretha
4. Photochemistry of Conjugated Polyalkynes
Sang Chul Shim
5. Photochemistry of Photophysics of Carbocations
Mary K. Boyd
6. Regio- and Stereoselective 2 + 2 Photocycloadditions
Cara L. Bradford, Steven A. Fleming, and J. Jerry Gao
7. Photoinduced Redox Reactions in Organic Synthesis
Ganesh Pandey
ix