Ebeid, El-Zeiny M.

El-Daly, Samy A.

Langhals, Heinz

English

Open Access LMU

J.  Phys. Chem. 1988,92,45654568 4565 Ftgure 18. A docription for the electron beam apparatus used for the electron beam exposures at atmospheric prc~rurer of dry nitrogen. that fraction of the beam backscattered from the substrate. The charge density is defined as Q = (1 + 1)q  where q is the backscattering coefficient of the substrate. All of our experimental results are reported in terms of Q because it is a more precise measure of the number of electrons traversing a thin film. Q is readily converted to adsorbed dose using the methodology outlined previously." Elecrron Beam Exposure Appararus for Exposures a1 Al- maipheric Pressures ofNilrogen. Electron beam exposure of the samples was achieved with a CR I SO Electron Processor (Energy Sciences, Inc.. Woburn, MA) which allows exposures of the samples in an atmosphere of nitrogen. A diagram of the apparatus is shown in Figure 18. Basically, the instrument consists of a shielded conveyor that transports the sample under an clcctron beam. Electrons emanating from a rodlike filament are accel- erated and subsequently exit through a Ti/AI alloy window to form a "planar" s h a d  electron beam perpendicular to the di- rection in which the samples moves. The electron beam gun operates a t  accelerating voltages between 150 and 175 kV. The dose delivered to the sample is controlled by adjusting either the beam current or the conveyor speed. The course of the electron beam induced decomposition was followed by using infrared spectroscopy. Infrared spectra of the solid thin film samples were coated on I-in.-diameter silicon substrates and recorded with a Perkin Elmer 580 IR spectrometer. The silicon substrates, obtained from Diode Corp., Framington, MA, are polished on both sides and are tapered (8-12 mil) to eliminate interference fringes. A bare silicon substrate was exposed to a 175-kV beam for doses up to 1000 Mrad with no new ab- sorptions appearing. Dosimetry was performed using the aminopbenolmethane dye doped films produced by Far West Technology, Goleta, CA. The thickness of the dosimetric films was 2 mil and the absorbed dose was measured by recording the optical density a t  510 nm before and after exposure as reported earlier.'l A silicon wafer was placed beneath the dosimetric film to obtain the fraction of the absorbed dose from backscattering of the electron beam. The absorbed dose in the sample was obtained by using the equations for stopping power of the sample and d0~imeter . l~  Samples of irradiated material in sufficient quantities for product analysis were prepared by using a tray made from a metal block into which a well, 3 mil deep and of area equal to 160 cm2, was machined. A viscous solution of material was placed in the tray to flood the well and, subsequently, the sample thickness was brought to 3 mil by pulling a straightedge across the sides of the well and the remaining solvent allowed to dry. After the sample was exposed to the 175-kV electron beam it was collected and stored in capped bottles for analysis. Regis- No. 1,5610-94-6; 2, 114885-79-9; 7,879-15-2; 8, 108-39-4; 9, 71-43-2; 2-nitro-I-naphthol, 607-24-9; 2-amino-I-naphthol hydro- chloride, 41172-23-0; sodium 2-diazo-l-naphth~quinone-5-sulfonate, 2657-00-3; 2-diazo-l-naphthaquinone-5-sulfonyl chloride, 1 10928-59-1. (13) Pacansky, J.: Wang,C.; Waltman,R. J. 1. FImrimChem. 1986.32. (14) Pacansky, I.: Waltman, R. I. 1. Rod. Curing 1986, 13. 24. 286. Emission Characteristics and Photostability of N,N'-Bis(2,5-di-tert-butylphenyl)-3,4:9,lO-perylenebis(dicarboximide) El-Zeiny M. Ebeid,* Samy A. El-Daly, Department of Chemistry, Faculty of Science, Tania Uniuersity, Tanta, Egypt and Heinz Langbals Instiiut fur Organische Chemie der Uniuersitdt Miinchen, Karlstrasse 23, 0-8000 Mtinchen 2, West Germany (Received: July 30, 1987: In Final Form: December 17. 1987) The titled dye (1) shows very high fluorescence quantum yield values as well as photostability. The dye undergoes molecular aggregation both in the ground state (at a critical concentration of ca. 2 X IO4 mol dm-l) and in the excited slate (giving excimerlike emission at ca. 600 nm). It displays solvatochromism in both emission and UV-visible absorption spectra. The dye does not give laser emission upon pumping ethanolic solutions with a nitrogen laser (& = 337.1 nm, peak power of 100 kW) but acts as an efficient quencher of 1,4-bis(@pyridyl-2-vinyl)benzene (P2VB) laser dye. The quenching process obeys a static type mechanism. Equimolar mixtures of dye 1 and P2VB or 2,5-distyrylpyrazine (DSP) laser dyes also give no laser emission. With even higher peak power (200 kW, pulse duration of 800 LIS) a laser emission can be obtained from chloroform solutions of dye 1. Introduetion The synthesis and spectral identification of several highly fluorescent and very highly stable perylene derivatives have been recently reprted.l Dyes of such unique characteristics are very attractive in many areas, e.g., dye lasers, and solar energy con- version, and can serve as photosensitizers, photon counters, and ( I )  Langhals, H. Chem. Be,. 1985,118,4641. 0022-3654/88/2092-4565$01.50/0  1988 American Chemical Society 

Emission Characteristics and Photostability of N,N'-Bis(2,5-di-tert-butylphenyl)-3,4:9,lO-perylenebis(dicarboximide)

Universität München: Elektronischen Publikationen

J.  Phys. Chem. 1988,92,45654568 4565 
Ftgure 18. A docription for the electron beam apparatus used for the 
electron beam exposures at atmospheric prc~rurer of dry nitrogen. 
that fraction of the beam backscattered from the substrate. The 
charge density is defined as 
Q = (1 + 1)q  
where q is the backscattering coefficient of the substrate. All of 
our experimental results are reported in terms of Q because it is 
a more precise measure of the number of electrons traversing a 
thin film. Q is readily converted to adsorbed dose using the 
methodology outlined previously." 
Elecrron Beam Exposure Appararus for Exposures a1 Al- 
maipheric Pressures ofNilrogen. Electron beam exposure of the 
samples was achieved with a CR I SO Electron Processor (Energy 
Sciences, Inc.. Woburn, MA) which allows exposures of the 
samples in an atmosphere of nitrogen. A diagram of the apparatus 
is shown in Figure 18. Basically, the instrument consists of a 
shielded conveyor that transports the sample under an clcctron 
beam. Electrons emanating from a rodlike filament are accel- 
erated and subsequently exit through a Ti/AI alloy window to 
form a "planar" s h a d  electron beam perpendicular to the di- 
rection in which the samples moves. The electron beam gun 
operates a t  accelerating voltages between 150 and 175 kV. The 
dose delivered to the sample is controlled by adjusting either the 
beam current or the conveyor speed. 
The course of the electron beam induced decomposition was 
followed by using infrared spectroscopy. Infrared spectra of the 
solid thin film samples were coated on I-in.-diameter silicon 
substrates and recorded with a Perkin Elmer 580 IR spectrometer. 
The silicon substrates, obtained from Diode Corp., Framington, 
MA, are polished on both sides and are tapered (8-12 mil) to 
eliminate interference fringes. A bare silicon substrate was exposed 
to a 175-kV beam for doses up to 1000 Mrad with no new ab- 
sorptions appearing. 
Dosimetry was performed using the aminopbenolmethane dye 
doped films produced by Far West Technology, Goleta, CA. The 
thickness of the dosimetric films was 2 mil and the absorbed dose 
was measured by recording the optical density a t  510 nm before 
and after exposure as reported earlier.'l A silicon wafer was 
placed beneath the dosimetric film to obtain the fraction of the 
absorbed dose from backscattering of the electron beam. The 
absorbed dose in the sample was obtained by using the equations 
for stopping power of the sample and d0~imeter . l~  
Samples of irradiated material in sufficient quantities for 
product analysis were prepared by using a tray made from a metal 
block into which a well, 3 mil deep and of area equal to 160 cm2, 
was machined. A viscous solution of material was placed in the 
tray to flood the well and, subsequently, the sample thickness was 
brought to 3 mil by pulling a straightedge across the sides of the 
well and the remaining solvent allowed to dry. After the sample 
was exposed to the 175-kV electron beam it was collected and 
stored in capped bottles for analysis. 
Regis- No. 1,5610-94-6; 2, 114885-79-9; 7,879-15-2; 8, 108-39-4; 
9, 71-43-2; 2-nitro-I-naphthol, 607-24-9; 2-amino-I-naphthol hydro- 
chloride, 41172-23-0; sodium 2-diazo-l-naphth~quinone-5-sulfonate, 
2657-00-3; 2-diazo-l-naphthaquinone-5-sulfonyl chloride, 1 10928-59-1. 
(13) Pacansky, J.: Wang,C.; Waltman,R. J. 1. FImrimChem. 1986.32. 
(14) Pacansky, I.: Waltman, R. I. 1. Rod. Curing 1986, 13. 24. 
286. 
Emission Characteristics and Photostability of 
N,N'-Bis(2,5-di-tert-butylphenyl)-3,4:9,lO-perylenebis(dicarboximide) 
El-Zeiny M. Ebeid,* Samy A. El-Daly, 
Department of Chemistry, Faculty of Science, Tania Uniuersity, Tanta, Egypt 
and Heinz Langbals 
Instiiut fur Organische Chemie der Uniuersitdt Miinchen, Karlstrasse 23, 0-8000 Mtinchen 2, West Germany 
(Received: July 30, 1987: In Final Form: December 17. 1987) 
The titled dye (1) shows very high fluorescence quantum yield values as well as photostability. The dye undergoes molecular 
aggregation both in the ground state (at a critical concentration of ca. 2 X IO4 mol dm-l) and in the excited slate (giving 
excimerlike emission at ca. 600 nm). It displays solvatochromism in both emission and UV-visible absorption spectra. The 
dye does not give laser emission upon pumping ethanolic solutions with a nitrogen laser (& = 337.1 nm, peak power of 
100 kW) but acts as an efficient quencher of 1,4-bis(@pyridyl-2-vinyl)benzene (P2VB) laser dye. The quenching process 
obeys a static type mechanism. Equimolar mixtures of dye 1 and P2VB or 2,5-distyrylpyrazine (DSP) laser dyes also give 
no laser emission. With even higher peak power (200 kW, pulse duration of 800 LIS) a laser emission can be obtained from 
chloroform solutions of dye 1. 
Introduetion 
The synthesis and spectral identification of several highly 
fluorescent and very highly stable perylene derivatives have been 
recently reprted.l Dyes of such unique characteristics are very 
attractive in many areas, e.g., dye lasers, and solar energy con- 
version, and can serve as photosensitizers, photon counters, and 
( I )  Langhals, H. Chem. Be,. 1985,118,4641. 
0022-3654/88/2092-4565$01.50/0  1988 American Chemical Society 


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Emission Characteristics and Photostability of N,N'-Bis(2,5-di-tert-butylphenyl)-3,4:9,lO-perylenebis(dicarboximide)

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