Near-Infrared Dyes for High Technology Applications PDF by Siegfried Daehne, Ute Resch-Genger and Otto S. Wolfbeis

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Near-Infrared Dyes for High Technology Applications
Edited by Siegfried Daehne, Ute Resch-Genger and Otto S. Wolfbeis
Near-Infrared Dyes for High Technology Applications

TABLE OF CONTENTS

(in capitals: correspondence author)
Preface ............................................................ ix
Advances in Methodology ..................... -........................ 1
Recent Developments in Fluorescence Spectroscopy: Three-Photon Excitation,
Two-Color Two-Photon Excitation, Light Quenching and Development of
Long-Lifetime Probes for Biophysics and Clinical Chemistry ................... 3
JOSEPH R. LAJ(OWICZ, Ignacy Gryzynski, Henryk Szmacinski,
Henryk Malak, Felix N. Castellano, Zakir Murtaza, Xiang-Qun Guo,
Li Li, Harriet Lin and Jonathan D. Dattelbaum
Near-Infrared Fluorescence Instrumentation for DNA Analysis ................ 21
LYLE MIDDENDORF, Jim Amen, Robert Bruce, Dan Draney,
Darryl DeGraff, John Gewecke, Dan Grone, Pat Humphrey,
Garrick Little, Ananda Lugade, Nara Narayanan, Abe Oommen,
Harry Osterman, Rex Peterson, John Rada, Ramesh Raghavachari
and Steve Roemer
Highlights in Biochemistry and Biophysics .............................. 55
Ultrasensitive Detection and Identification of Biomolecules with Diode
Lasers - from DYES to DNA ........................................... 57
M Sauer, K.H. Drexhage, D. Herten, U. Lieberwirth, R. Maller,
M Neumann, S. Nord, S. Siebert, A. Schulz, C. Zander and
J. WOLFRUM
Incorporation of Dye in Resting and Stimulated Leukocytes ................... 87
DANUTA FRACKOWIAK, Alfons Planner, Rodica-Mariana Ion and
KrzysztoJ Wiktorowicz
Application of Red Fluorescent Probes for the Measurement of Individual
Cell Cytoplasmic pH Values ........................................... 115
JAN SLA VIK
Molecular Probes Based on Cyanine Dyes for Nucleic Acid Research .......... 125
TODOR G. DELIGEORGIEV
New NIR Dyes: Synthesis, Spectral Properties and Applications in DNA
Analyses 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 141
NARASIMHACHARI NARAYANAN, Garrick Little, Ramesh Raghavachari,
Jasmin Gibson, Ananda Lugade, Chuck Prescott, Kevin Reiman,
Steve Roemer, Dave Steffens, Scott Sutter and Daniel Draney
Frontiers in Analytical Chemistry and Sensor Technology ................ 159
Luminescent Probes for NIR Sensing Applications 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 161
Eo Terpetschnig and o.s. WOLFBEIS
NIR Fluorophores in Practical Analytical Chemistry 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 183
Anan Ro Swamy, Abraham George, Leila A. Tarazi, GABOR PATONAY
and Lucjan Strekowski
Long Wavelength Emitting Fluorescence Probes for Metal Ions 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 191
K Rurack, J.L. Bricks, J.L. Slominskii and U RESCH-GENGER
Advances in High Technology Applications ..•...•.....•.•.....•.•.....• 201
NIR Dyes for Information Recording, from Origin to Update 0 0 0 0 0 • 0 0 0 0 0 0 0 0 • 0 0 203
MASARU MATSUOKA
Tuning of Color by Different Alignment of Dye Molecules 0 0 0 0 0 0 • 0 0 0 0 0 0 0 0 0 0 0 233
LARS DA'HNE and Erwin Biller
Spectral Sensitization of Silver Halides in NIR Region o. 0 0 0 0 0 0 0 •• 0 0 0 0 0 0 0 •• 0 • 243
Bol SHAPIRO
Optical Properties and Applications of Near Infrared Dyes in Polymeric
Media 00000000000000000000000000000000.00. 0 0 0 0.000000000000000.0.0265
0. v: PRZHONSKA
Insolubilisation and Fluorescence, Induced by Laser Diode Irridiation
ofIR-Dyes Embedded in Polymer Films. Thermally Induced Latex
Coalescence and Acid Generation 0 0 0 0 0 0 0 0 0 0 • 0 0 • 0 0 0 0 • 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 287
CDo Catry, C Jackers, J. Ronsmans, L. Bastin, PoCM Grim
and F.C DE SCHRYVER
NIR Photo sensitizers in Photodynamic Therapy 0 0 0 0 0 0 0 0 • 0 0 0 0 .00 0 • 0 • 0 0 0 • 0 •• 0 307
E.A. LUKYANETS
New Chromophores ....•.•.......•..•....•..................•...... 325
Molecular Engineering ofNIR Dyes .................................... 327
SIEGFRIED DAEHNE and Marina L. Dekhtyar
New NIR Dyes Based on the Cyclopentadienylium Chrom,ophore and
Related Compounds ................................................. 363
R. GOMPPER, A. Beck, T. Gessner, K. Hartmann, D. Heindl,
K. Polborn, R. Klinger and K. Yokogawa
New Cyanine Dyes Absorbing in the NIR Region .......................... 385
A.I. TOLMACHEV, Yu.L. Slominskii and A.A. Ishchenko
Near-Infrared Cyanine Dyes: A New Approach to an Old Problem ............. 417
Yu.L. BRICKS and N.N. Romanov
Adventures in Search of New Dyes Absorbing in the Red or Near Infrared
Region ............................................................ 427
HORST HARTMANN
Subject Index ...................................................... 445

Preface
This book summarizes the results of the NATO Advanced Research Workshop on "Syntheses, Optical Properties, and Applications of Near-Infrared (NIR) Dyes in High Technology Fields" held at Trest (Czech Republic) from September 24 to 27, 1997. It was attended by 52 scientists from 16 countries, among them 18 participants from 8 Eastern-Europe.

The Workshop has been stimulated by the great progress that has been made in utilizing NIR dyes in high technology areas. This has been triggered by the availability of reliable. vel)' small, and inexpensive laser diodes emitting in the NIR region which raise the analytical detection limits by several orders of magnitude, allow time-resolved measurements for temporal discrimination between spectrally similar species, and make possible miniaturization as well as remote sensing through space and by fiber optical techniques. Furthermore, NIR dyes proved to be vel)' important in other high technology fields such as laser physics, optical recording techniques, nonlinear optics, biochemistty and medicine.

The following contributions summarize the latest results of relevant topics which are addressed to both scientists and engineers who are interested in high technology applications of NIR dyes. The Workshop was organized by the members of the Scientific Committee, S. DAEHNE (Berlin), J. SLAVIK (Prague), O. S. WOLFBEIS (Regensburg) and A. I. TOLMACHEV (Kiev). It was made possible by the generous financial support of several sponsors. In addition to the main fund provided by the NATO SCIENTIFIC and ENVIRONMENTAL AFFAIRS DIVISION, the support of the following sponsors is gratefully acknowledged: ALLIED SIGNALS, RIEDEL-DE HAEN (Seelze), BOEHRINGER-MANNHEIM (Tutzing), FEW FORSCHUNGS- und ENTWICKLUNGSGESELLSCHAFT WOLFEN (Wolf en), LI-COR (Lincoln, Nebraska), and NYCOMED (Wayne, PA). Their support greatly helped to cover the expenses necessaty for organizing an AR W that unified scientists from East and West. ,

The scientific output of the meeting was substantial. Advances in methodology are reported that are concerned with new laser spectroscopic techniques in order to improve the sensitivity and specifity of analytical methods, to reduce noise from background and autofluorescence of the samples to be analyzed, to extend the range of time-resolved fluorescence deteCtion and to enable fast and reliable routine analyses through fully automated instrumentation, especially for bioanalyses like DNA-sequencing, inununoassays, cytology, membrane analyses, and environmental bioanalyses.

No other analytical method known so far can compete with the sensitivity of single molecule detection which is now possible using laser-induced fluorescence. The progress reached via these developments is described in highlights in biochemistry and biophysics where NIR dyes currently are extensively used. The ongoing human genom project is one of the great challenges of mankind.

Luminescent probing and labeling for the analytical determination of metal ions, anions, pH values, and environmental pollutants belong to the frontiers in analytical chemistry and sensor technology likewise. Again, NIR dyes have made possible a progress never achieved.

Other recent advances in high technology applications include, for instance, infonnation recording techniques like xerography, photoresists, thermal transfer printing, laser printers, optical cards, transparent bar-codes, forgery prevention, optical disks, and CDs. A promising new application is color tuning of thin films via different alignment of dye molecules. Spectral sensitization of NIR sensitive photographic silver halide films is now possible up to 1600 nm. The hitherto used liquid solutions for tunable NIR dye lasers can be substituted by solid organic polymers. The mechanisms of polymerization and coalescence of latex can be elucidated by means of NIR dyes. Last, but not least, great progress has been achieved through application of NIR dyes in photodynamic therapy of cancer.

Another area of intense activity deals with the search for thermally and photochemically stable new chromophores having strong absorption and emission in the NIR region. The design of new dyes based on theoretical considerations is meanwhile as important as are synthetic efforts. New chromophores have been designed, and substantial progress has been made with respect to the synthesis of new dyes of the well-known cyanine type.

The organizers wish to express their thanks to all participants for having reached the balance between competence and communication throughout the workshop. The nice ambience of the Castle Hotel Trest, owned by the Czech Academy of Sciences, and its staff further contributed to the success of the meeting.
 
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