Highlights vol.5, 1


The Xerographic Process.
An Application of Photoinduced Electron Transfer in the Office

The term xerography originates from the Greek words xero and graphos, which together mean "dry writing". In the early thirties, out of the need for making carbon copies of legal documents in his own work, the inventor of xerography, Chester Carlson, envisioned the benefit of having a copying machine in the office. He studiously examined various light-related electrostatic phenomena. In 1938, he filed the first patent on what he called electrophotography.1 Using evaporated thin films of sulfur and anthracene as photoconductors, Carlson was able to demonstrate the essence of xerography, that is the photogeneration of electrostatic images and the development of these images on paper. The road of commercialization of the xerographic process was quite dramatic.2 The process was reduced to practice in 1949 through the Xerox Model A copier and became fully automated in 1959 in the Xerox Copier Model 914. Model 914 was one of the most successful single products in the history of business. It not only turned the small photographic company, Haloid, into a giant corporation, Xerox, but also revolutionized the way modern offices work, making copier machines a non-disposable, integral part of office appliances today. With the recent advances of laser and computer technologies, xerography is no longer limited to making duplication, it also creates the document.

The basic steps in the xerographic process are depicted in Figure 1. The process involves charging (steps 1 and 2) and imagewise photodischarging (step 3) of the photoreceptor. The photogenerated electrostatic images are then developed by toner (or dry ink) electrostatically (steps 4 and 5). After transferring the toned images to paper (step 6), the images are then fused to produce a photocopy.

Figure 1: Basic steps in the xerographic process.

A single layer of amorphous selenium was used as the photoconductor in earlier copier products. For cost and performance reasons, recent research has been focused on the use of organic materials in a bilayer device configuration. In bilayer photoreceptor devices, the charge generation and the charge transporting functions are separated into two discrete layers, the CGL for generating the charges and the CTL for transporting the charges.3 Since the technology of hole transporting molecules is more advanced than that of electron transporting molecules, most practical photoreceptors today are negatively charged at the surface. The configuration and the imaging mechanism of a bilayer photoreceptor device is given in Figure 2.

Figure 2: Schematics of the configuration and the photodischarge process of a bilayer photoreceptor (CGL: charge generation layer; CTL : charge transporting layer)

Illumination of the bilayer device results in the formation of electron-hole (e-h) pairs in the CGL. The photogenerated holes inject to the CTL, wherein these holes migrate across the device to form the intended electrostatic images. In the last decade, many classes of organic photoconductors, such as phthalocyanines, squaraines, azo pigments, perylenes, etc. have been successfully developed for photoreceptor application. The structures and the photoconductivity of these materials are currently being reviewed by Kock-Yee Law (Xerox) in an article prepared for Chemical Reviews. Partly due to experimental difficulties and partly due to the rapid pace of technology development in industry, research efforts have been concentrated on the development of better or new materials and devices. Not enough attention has been paid to the basic sciences of the photodischarge process. Interesting research areas, such as molecular and architectural effects on photogeneration, and factors that affect the charge recombination of organic photoconductors and the subsequent interfacial electron transfer processes, remain to be explored.

In one of the Center projects, Kock-Yee Law and David G. Whitten (UR) attempt to use molecular aggregates assembled by Langmuir-Blodgett (LB) film techniques to investigate the fundamental processes of photogeneration and electron transfer in organic photoconductors. Surfactant squaraines 1-3, which were designed to orient the "brick-like" squaraine chromophore in three different orientations when organized as monolayers, have been synthesized.4

Figure 3: Structures and orientations (at air-water interface) of surfactant squaraines.

Surface pressure-area isotherms show that the squaraine chromophores in 1-3 orient on water as designed. The monolayers of 1 and 2 have been transferred to glass substrates. The absorption spectra of 1 and 2 in LB films, which are different from their solution spectra, are also different from each other (Figure 4). The absorption spectra suggest that the squaraine chromophores in the LB films of 1 and 2 form different aggregates and that there is an orientation effect on the aggregation. The stacking arrangements of the aggregates are given in the insert of Figure 4 based on absorption and structural data obtained from microcrystalline squaraine compounds.

Figure 4: Absorption spectra of (a) LB film of squaraine 1 and (b) LB film of squaraine 2 on glass (inset: solution absorptions in chloroform and schematics of intermolecular interactions of the squaraine chromophores in LB films).

Now, a photoelectrochemical apparatus has been set up in the center by Young-Soon Kim (CPCT) to examine the photoconductivity of these aggregates. Preliminary experiments using a monolayer of 1 on SnO2-glass substrates indicate that both cathodic and anodic photocurrents can be observed and that the spectral response parallels the absorption of the aggregate in Figure 4a. These initial findings offer numerous possibilities for further experimentation, where fundamental issues related to the stacking arrangement, orientation and inter site distance of the chromophore on the photogeneration efficiency and the subsequent electron transfer process can be addressed.

References

1. Carlson, C.F. U.S. Patent 2, 221,776, 1940.
2. Mort, J. The Anatomy of Xerography. Its Invention and Evolution; McFarland & Co. Inc., London, 1989.
3. Melz, P.J.; Champ, R.B.; Chang, L.S.; Chiou, C.; Keller, G.S.; Liclican, L.C.; Neiman, R.B.; Shattuck, M.D.; Weiche, W.J. Photogr. Sci. Eng. 1977, 21, 73
4. Law, K.Y.; Chen, C.C. J. Phys. Chem. 1989, 93, 2533.


4th ANNUAL SYMPOSIUM ON PHOTOINDUCED CHARGE TRANSFER

July 21-23, 1993
The Center symposia alternate between general and more specialized themes related to photoinduced charge transfer. This year's symposium is a specialized one on the subject of Electron Transfer in Homogeneous Media focusing on three main themes:


This year's conference organizers are Professor Joseph Dinnocenzo (UR), Professor Joshua Goodman (UR) and Dr. Ian Gould (Kodak). A conference registration form and a tentative program are included in this issue. If you would like more information, please contact the Center at (716) 275-8286.


REGISTRATION INFORMATION FOR THE 4TH ANNUAL SYMPOSIUM

To pre-register for the Conference, return the registration form with the pre-registration fee of $125.00 ($25.00 for graduate students). PARKING ON CAMPUS - It is a 10 minute taxi ride from the Rochester International Airport to the University of Rochester. The University dormitory is a short walk from Hutchison Hall. A permit for parking on campus will be arranged if requested on the registration form. HOUSING : Campus Dormitory. Housing is available in the Towne House. You may reserve a room on the pre-registration form. It is approximately $26 per night for a single room. This rate includes all linens. The dorms are cleaned one time per week.;
Off-Campus Hotels. Blocks of rooms are being held for the Conference at the Comfort Inn and the Marketplace Inn until June 19. In order to receive the rate listed on the pre-registration form, we need to make your reservation for you. Please be sure to circle the dates for which you will require accommodations.


NEW INDUSTRIAL PROGRAM

The Center is exploring possibilities for sabbatical programs for visitors from industry. These special fellows would work on collaborative research projects for a period from six months to a year or longer (a list of our current projects is on pg. 11). We would be happy to receive suggestions as we formulate this program, as well as inquiries from possible participants. Please call David G. Whitten, Director (716) 275-1858 or Debbie Shannon, (716) 275-8286 if you have any suggestions or questions.


TWO PATENT APPLICATIONS FILED

Some specific highlights of last year's activities include two patents being filed which were a result of joint Xerox-University of Rochester activities in the area of conducting polymers. The joint work leading to the first patent has been widely publicized in the popular technical press, the Wall Street Journal and in an NSF "Knowledge Transfer" publication. This project is also featured in a video prepared for Japanese TV. A second patent application on BBL, unrelated to the first, has also been filed.


INTERNATIONAL COLLABORATIONS

The Center has also been involved in a number of activities involving international cooperation. A highlight of this was a binational workshop co-hosted by the Center and the Institute of Photographic Science of Academia Sinica in Beijing in September '92. The workshop was funded by a grant from the International Division of NSF and featured a series of talks by both US and Chinese investigators in an informal setting which promoted maximal discussion of several projects in the area of photoinduced charge transfer. This workshop was highly stimulating scientifically and provided the US participants a good picture of the extremely rapid research progress that China has made in this area during the past 5-10 years. It also laid ground for future collaborations between the two countries with a focus on center-to-center cooperation that should be mutually fruitful. We have had considerable contact with similarly focused research centers in Japan. Formal collaborative activities with Japan will begin as early as this July 1993 when three Center Graduate Students begin collaborative research at the Institute for Molecular Science in Okazaki, Japan. If you would like more information regarding these programs, please contact David Whitten or Debbie Shannon in the Center at (716) 275-8286.


VISITING SCIENTISTS

Professor Kazuhiro Nakasuji, Institute for Molecular Science, Japan, visited the Center March 16 and 17, 1992.

Professor A.K.M Hoque, Lane College, located in Jackson, TN, spent Summer '92 doing research with Professor J.P. Dinnocenzo

Professor M. Kojima, Shinshu University, Japan, collaborated on a Center Project involving Professors Dinnocenzo and Goodman of the University of Rochester and Drs. Farid and Gould of the Eastman Kodak Co.

Dr. T. Takagahara, NTT, Japan, visited the Center on October 15, 1992.

Dr. Shobatake, Institute for Molecular Science, visited the Center on March 2, 1993.


CENTER OUTREACH ACTIVITIES

NEW OUTREACH PROGRAM!!

The Center has just received additional funding from the National Science Foundation to host faculty sabbaticals and undergraduate students from Historically Black Colleges and Universities (HBCUs) to collaborate on Center research. This Program will begin Summer '93 with Dr. A.K.M. Hoque from Lane University in Jackson, TN. If you know of faculty who would be interested in this Program or would like more information about it, please contact Professor Jack A. Kampmeier at (716) 275-4441.

The NSF Science & Technology Center's Summer Research Program for High School and Community College Teachers once again demonstrated its mutually beneficial interaction between high school teachers and research groups during the Summer 1992. This year's constituent was made up of nine high school teachers and one community college teacher. Six came from the Rochester area (Gordon Dorway, Franklin High School; Richard Hendricks, Joseph Wilson Magnet High School; Linda Hobart, Finger Lakes Community College; Donald Horner, Fairport High School; Claude Meyers, Greece Arcadia High School; and Carl Thielking, Fairport High School) and four from a national pool (Ernest Harrington, Staples High School in Westport, CT; John Lilga, Thomas S. Wooton High School in Rockville, MD; David Rader, The Indiana Academy in Muncie, IN; and M. Gwen Siebert, The Governor's School in Roanoke, VA). In addition, one of the 1991 teachers, Ed Hull, returned to the project in 1992 with special supplementary funding from NSF.

Their primary focus was hands-on scientific research. Our view is that this is the best possible continuing education for a professional teacher of science; the responses of the teachers confirm the exceptional value of the experience. Teachers also participate in a short course and a weekly group meeting at which they present and discuss their research plans and accomplishments for each other. Several of these group meetings turned into discussions about teaching. One of the meetings brought our university teachers of freshman chemistry together with the visiting teachers. The quality of the 1992 teachers was dazzling. We have received additional funding from the National Science Foundation and will host eleven teachers in Summer '93. Anyone interested in more information about this program should contact Professor Jack Kampmeier (716) 275-4441 or Debbie Shannon (716) 275-8286.

A photo of the 1992 group is shown below.

Left to right: C. Meyers, K. Thielking, E. Hull, D. Shannon, J. Lilga, R. Hendricks, G. Dorway, J. Kampmeier, D. Horner, L. Hobart, K. Loos, E. Harrington, M.G. Siebert, D. Rader

The Scanning Tunneling Microscope loaner library started its circulation in December '92. The Center was able to purchase a 486 computer to circulate with the high school loaner STM with supplemental funding from the Xerox Corp. The instrument has been circulated to nine high schools locally and two in the Washington, DC area. Two other STMs have also been circulated to eight colleges in the DANA program for use in undergraduate research and education.


CENTER VIDEO

The most recent activity which the Center has undertaken is the production of a video to inform the public of the collaborations taking place between academic and industrial researchers. Our intention is to make a larger audience aware of these unique collaborations ongoing in the Center for Photoinduced Charge Transfer. It is planned to be finished by mid-July for its debut presentation at the Montage Conference. For more information, please call the Center (716) 275-8286.


Photoinduced Charge Transfer Course
CHM 552: Topics in Chemical Physics: Photoinduced Charge Transfer was offered during the Spring '93 semester. If you would like copies of the notes or have questions concerning this course, contact Professor George McLendon (275-5751) or Debbie Shannon at the Science and Technology Center (275-8286).

The course provides an overview of the fundamentals of photoinduced charge transfer in solution and the solid state, focusing on key technologies associated with the NSF Science and Technology Center.

A list of the topics presented follows:


CONGRATULATIONS!!

Dr. Esther Conwell received an honorary D.Sci from Brooklyn College of CUNY and was also elected to the American Academy of Arts and Science Professor George McLendon won the 1992 ACS Akron Section Award Professor R. J. Dwayne Miller received a Guggenheim Fellowship for 1992-93

Professor Anne Myers received a 1992 Dreyfus Teacher Scholar Award


CENTER PROJECT RENEWALS

An External Review Committee consisting of Dr. David Eaton, DuPont (Chair), Dr. Raymond Baughman (Allied Signal), Professor Arthur Ellis (U. Wisconsin), Professor Cliff Kubiak (Purdue), and Dr. Mike Steigerwald (AT&T Bell Labs) met on Saturday, May 30, 1992 to review seven Center Project Renewals. After making their recommendations, the Center Council (Dean R. Aslin, Dr. Leonard Brillson, Dr. Esther Conwell, Professor R. Eisenberg, Dr. Samir Farid, Professor Jack Kampmeier, Professor Andrew Kende, Dr. Frank Lovecchio and David Whitten) met on Wednesday, June 10, 1992. In addition, the Center received and reviewed two new proposals which were funded in April, 1993. A list of the current Center projects is on pg 11.

We have sent out the announcement for the '93 proposal renewals and "Call for Proposals" with a due date of May 21, 1993. The External Review Committee will review these proposals on Saturday, July 24. If you would like more information, you may contact Debbie Shannon at (716) 275-8286.


EXTERNAL ADVISORY BOARD

The Center's External Advisory Board met on February 11, 1993 to review the Center's progress and make recommendations for future directions. We have expanded our Board to include the following distinguished scientists:
Allen Bard, University of Texas at Austin
Robin Hochstrasser, University of Pennsylvania
Angelo A. Lamola, Rohm & Haas
Rudolph Marcus, California Institute of Technology
Thomas J. Meyer, University of North Carolina
Richard Quisenberry, E.I. duPont de Nemours and Co., Inc.
Norman Sutin, Brookhaven National Laboratory
John Tully, AT&T Bell Laboratories
C. Grant Willson, Almaden Research Center

If you would like a copy of this report please contact the Center at (716) 275-8286.


SEMINARS

Dr. John Facci, Xerox Corporation and Dr. Jerome Lenhard, Eastman Kodak Co., "Other Voltammetries: Potential Step, Pulsed, Square Wave and A.C. Techniques" CHM 593 (February, 1992)

Professor Keith Oldham, Trent University, "Extracting Kinetic Information from Voltammetric Data", (March, 1992)

Professor Dwight Sweigart, Brown University, "Applications of Voltammetry to Organometallic Chemistry" (March, 1992)

Professor Michael Kuzmin, Moscow University, "Proton Transfer Photoreactions in Organized Molecular Systems: Exciplex Mechanism of Fluorescence Quenching in Polar Media" (March, 1992)

Professor Dennis Evans, University of Delaware, "Mechanisms of Organic Electrochemical Reactions" (March, 1992)

Professor Fred Lewis, Northwestern University, "Applications of Photoinduced Charge Transfer to the Synthesis of Nitrogen Heterocycles" (April, 1992)

Professor Hiroshi Masuhara, Osaka University, "Laser Manipulation, Spectroscopy, and Photochemistry of Polymer Microspheres in Solution" (April, 1992 at Kodak)

Professor Chris Foote, University of California at Los Angeles, "Photoinduced Electron Transfer in Fullerenes and other Photochemical Reactions" (April 1992)

Professor A. Vlcek, Jr., J. Heyrovsky Institut of Physical Chemistry and Electrochemistry, Prague, Czechoslovakia, "Redox Chemistry and Spectroelectrochemistry of Mn and Re Dioxolene Complexes" (April, 1992)

Professor Michael Kasha, Florida State University, "Excited State Electron Transfer and Proton Transfer in Molecular Probes", and "From Flower Pigments to the Proton-Transfer Laser (at Kodak, May 1992)

Professor Anthony F. Garito, University of Pennsylvania, "Excited State Enhancement Mechanism for Nonresonant Nonlinear Optical Responses" (May, 1992)

Dr. Klaas Zachariasse, Max Planck Institut für Biophysikalische Chemie, "Intramolecular Charge Transfer in Aminobenzonitriles" (August, 1992)

Professor Philipp Gütlich, Institut für Anorganische Chemie, Johannes-Gutenberg-Universität, "Thermal- and Light-Induced Switching of Iron (II) Coordination Compounds" (September 1992)

Dr. Urs Wild, ETH-Zurich "From Single Molecule Spectroscopy to the Molecular Computer" (October 1992)

Professor Daniel Wayner, National Research Council of Canada, "Reactions of Ketyl and 1,3-Dioxolanyl Radicals with Electron Deficient Bromides: Electron Transfer or Atom Transfer" (October, 1992)

Dr. Victor Kanarov, State University of Tashkent, USSR, "Influence of Electron Structure on a Electron Transfer on Atom-Solid Collisions" (December, 1992)

Professor Andre Braun, University Karlsruhe, "Application of Xe-Excimer Lamps in the Oxidation Degradation of Organic Water Pollutants" (December, 1992)

Professor Roland Zimmerman, Humboldt-Universitätat zu Berlin, "Excitons in Semiconductor Quantum Structures" (January, 1993)

Professor Gertz Likhtenshtein, Ben Gurion University, Israel, "Factors Affected Electron Transfer in Proteins Modified by a Donor-Acceptor Pair: Dynamics, Micropolarity, and Orbital Overlap" (March, 1993)

Professor Nenad M. Kostic, Iowa State University, "Electron Transfer Between Cytochrome c and Plastocyanine: Evidence for Protein Dynamics" (March, 1993)

Professor E. Guy Wilson, Queen Mary and Westfield College, London, "Control of Electron Transfer in Nanostructure Assembled from Organic Molecules" (April, 1993)

Dr. David Citrin, Max-Planck-Institute, "Theory of Excitons in Low-Dimensional Semiconductor Structures: Polaritons and Radiative Decay" (April, 1993)


The Center Highlights

is published by the NSF Center for Photoinduced Charge Transfer at the University of Rochester, Rochester, NY 14627-0219

David G. Whitten, Director
Samir Farid, Associate Director
Jack Kampmeier, Associate Director
Esther Conwell, Associate Director
Kenneth Simolo, Assistant Director
Debbie Shannon, Administrative Assistant

TEL. (716) 275-8286
FAX (716) 473-6889

May 1993, Vol. 5, No. 1

University of Rochester
NSF Center for Photoinduced Charge Transfer
Department of Chemistry
200 Hutchison Hall
Rochester, NY 14627