Infrared Absorbing Dyes

230 Pages·1990·6.13 MB·English

by  Masaru Matsuoka (auth.)

Infrared Absorbing
Dyes
TOPICS IN APPLIED CHEMISTRY
Series Editors: Alan R. Katritzky, FRS
Kenan Professor of Chemistry
University of Florida. Gainesville. Florida
Gebran J. Sabongi
Laboratory Manager, Encapsulation Technology Center
3M, St. Paul. Minnesota
BIOCATALYSTS FOR INDUSTRY
Edited by Jonathan S. Dordick
CHEMICAL TRIGGERING
Reactions of Potential Utility in Industrial Processes
Gebran J. Sabongi
THE CHEMISTRY AND APPLICATION OF DYES
Edited by David R. Waring and Geoffrey Hallas
HIGH-TECHNOLOGY APPLICATIONS OF ORGANIC COLORANTS
Peter Gregory
INFRARED ABSORBING DYES
Edited by Masaru Matsuoka
STRUCTURAL ADHESIVES
Edited by S. R. Hartshorn
A Continuation Order Plan is available for this series. A continuation order will bring delivery of
each new volume immediately upon publication. Volumes are billed only upon actual shipment. For
further information please contact the publisher.
Infrared Absorbing
Dyes
Edited by
Masaru Matsuoka
University of Osaka Prefecture
Sakai, Osaka, Japan
Springer Science+Business Media, LLC
Library of Congress Cataloging-ln-PublIcation Data
Infrared absorbing dyes / edited by Masaru Matsuoka.
p. cm. — (Topics in applied chemistry)
Includes bibliographical references and index.
ISBN 978-1-4899-2048-5
1. Dye lasers—Materials. I. Matsuoka, Masaru, 1942-
II. Series.
TA1690.153 1990
621.36' 2—dc20 90-40052
CIP
ISBN 978-1-4899-2048-5 ISBN 978-1-4899-2046-1 (eBook)
DOI 10.1007/978-1-4899-2046-1
© 1990 Springer Science+Business Media New York
Originally published by Plenum Press, New York in 1990
Softcover reprint of the hardcover 1st edition 1990
All rights reserved
No part of this book may be reproduced, stored in a retrieval system, or transmitted
in any form or by any means, electronic, mechanical, photocopying, microfilming,
recording, or otherwise, without written permission from the Publisher
Contributors
David Dolphin, Department of Chemistry, University of British Columbia,
Vancouver, British Columbia, Canada V6T 1Y 6
Atsushi Kakuta, Hitachi Research Laboratory, Hitachi Ltd., Hitachi-shi,
Ibaraki-ken, 319-12, Japan
Fumio Matsui, Corporate Research and Development Laboratory, Pioneer
Electronic Corporation, Tsurugashima-machi, Iruma-gun, Saitama
350-02, Japan
Masaru Matsuoka, Department of Applied Chemistry, College of Engineer
ing, University of Osaka Prefecture, Sakai, Osaka 591, Japan
Yuji Mihara, Ashigara Research Laboratories, Fuji Photo Film Co., Ltd.,
Minami-Ashigara, Kanagawa 250-01, Japan
Yoshiharu Nagae, Hitachi Research Laboratory, Hitachi Ltd., Hitachi,
Ibaraki 319-12, Japan
Kenryo Namba, Advanced Materials Research Department, R& D Center,
TDK Corporation, Ichikawa, Chiba 272, Japan
Jun'etsu Seto, Research Center, SONY Corporation, Hodogaya-ku,
Yokohama, Kanagawa 240, Japan
Ethan Sternberg, Department of Chemistry, University of British Columbia,
Vancouver, British Columbia, Canada V6T 1Y 6
v
vi Contributors
Yoshiaki Suzuki, Late of Ashigara Research Laboratories, Fuji Photo Film
Co., Ltd., Minami-Ashigara, Kanagawa 250-01, Japan
Tadaaki Tani, Ashigara Research Laboratories, Fuji Photo Film Co., Ltd.,
Minami-Ashigara, Kanagawa 250-01, Japan
Masayasu Ueno, Opto-Electronics Research Laboratory, NEC Corporation,
Miyamae-ku, Kawasaki, Kanagawa 213, Japan
Tonao Yuasa, Opto-Electronics Research Laboratory, NEC Corporation,
Miyamae-ku, Kawasaki, Kanagawa 213, Japan
Preface
New laser technology has developed a new dye chemistry! Development
of the gallium-arsenic semiconductor laser (diode laser) that emits laser
light at 780-830 nm has made possible development of new opto-electronic
systems including laser optical recording systems, thermal writing display
systems, laser printing systems, and so on. Medical applications of lasers
in photodynamic therapy for the treatment of cancer were also developed.
In such systems, the infrared absorbing dyes OR dyes) are currently used
as effective photoreceivers for diode lasers, and will become the key materials
in high technology. At the present time the chemistry of IR dyes is the most
important and interesting field in dye chemistry.
Laser light can be highly monochromatic, very well collimated, coher
ent, and, in some cases, extremely powerful. These characteristics make
diode lasers a very cheap, convenient, and useful light source for a variety
of applications in science and technology. For these purposes, however, IR
dyes with special characteristics are required. To develop new IR dyes, it
is most important to establish the correlation between the chemical structures
of dyes and other characteristics of dyes, such as their absorption spectra.
Molecular design of IR dyes predicting the Amax and Emax values by
molecular orbital (MO) calculations is now possible even by using a personal
computer, and many types of new IR dyes have been demonstrated. Also,
new opto-electronic systems using IR dyes as photoreceivers have been
reported recently.
This book reviews the synthesis and characteristics of IR dyes and their
applications in high technology. In Chapter 2, synthetic design of IR dyes
by means of the PPP MO method is described. General methodology for
the molecular design of IR dyes is demonstrated for each of the
chromophoric systems. In the following six chapters, synthesis and charac
teristics of IR dyes from cyanine, quinone, phthalocyanine, metal com-
vii
viii Preface
plexes, and miscellaneous chromophores are described together with photo
chromic dyes. Chapter 9 deals with semiconductor lasers as a light source,
and the remaining chapters deal with the applications of IR dyes in optical
recording systems (Chapter 10), thermal writing displays (Chapter 11), laser
printing systems (Chapter 12), laser filter systems (Chapter 13), infrared
photography (Chapter 14), and medical applications (Chapter 15). In these
chapters, the up-to-date results and technology are included and many
figures are added for better understanding.
This book is intended mainly for color chemists, organic chemists, and
material scientists. It is hoped that it will also be useful for postgraduate
students in chemistry and material science.
It is a pleasure to gratefully acknowledge the contributors of each
chapter. Without their hard work and kind cooperation, this book could
not have been published in a timely manner. I also would like to record
my special gratitude to the late Mr. Yoshiaki Suzuki who died shortly after
the submission of his manuscript.
Finally, I would like to give my sincere thanks to Dr. John Griffiths
of the University of Leeds, and the Series Editors, Drs. G. Sabongi and A.
Kratitzki, who recommended me as an editor of this volume. I am also
grateful to Miss Kazuko Shirai for her skilled assistance in preparing the
manuscript.
Masaru Matsuoka
Osaka, Japan
Contents
Chapter 1. Introduction 1
Masaru Matsuoka
Part I. Synthesis and Characteristics of Infrared Absorbing Dyes
Chapter 2. Synthetic Design of Infrared Absorbing Dyes 7
Masaru Matsuoka
I. Introduction ..................... 7
II. PPP MO Method . . . . . . . . . . . . . . . . . .. 8
III. Synthetic Design of Infrared Absorbing Dyes by the PPP MO 9
Method .................. .
A. Intramolecular Charge-Transfer Chromophores 9
B. Intermolecular Charge-Transfer Chromophores 13
C. Cyanine Chromophores 14
References . . . . . . . . . . . . . . . . . . 17
Chapter 3. Cyanine Dyes 19
Masaru Matsuoka
I. Introduction ..... . 19
II. General Synthetic Method 20
III. Chromophoric Systems 22
IV. Heptamethinecyanines . . 24
V. Squarylium and Croconium Dyes 29
VI. Pyrylium and Related Dyes 31
References . . . . . . . 33
ix