Novel naphthalene diimides and a cyclophane thereof: synthesis

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FLUORESCENCE QUENCHING BETWEEN STRONG PI-ELECTRON
DONOR-ACCEPTORS OF CARBAZOLOCARBAZOLE AND
TETRANITROFLUORENONE LEADING TO ELECTRON TRANSFER
Icli S, Icil H, Whitten DG, Sayil C, Dityapak I
JOURNAL OF LUMINESCENCE
75 (4): 353-359 DEC 1997
Abstract:
Singlet energies and fluorescence quantum yields of synthesized dihydrocarbazolocarbazole,
1, dimethylcarbazolocarbazole, 2, dibenzylcarbazolocarbazole, 3, were measured to be
between 76.5-74.3 kcal/mol and 0.07-0.02 respectively. A Stern-Volmer plot of fluorescence
quenching of dihydrocarbazolocarbazole, 1, with 2,4,5,7-tetranitrofluorenone, 4, has given a
rate constant of quenching of kq = 7.4 x 1012 M-1s-1. The free energies of the exothermic
electron transfer reaction are calculated to be -33.6 kcal/mol for dihydrocarbazolocarbazole,
1, and -26.8 kcal/mol for dimethylcarbazolocarbazole, 2. High values for the rate of
fluorescence quenching and the free energies are the evidence for an electron transfer process
between these strong pi-electron donor-acceptor complexed molecules.
Author Keywords:
charge-transfer complexes, photoelectron transfer, triplet exciplex, carbazolocarbazole,
tetranitrofluorenone
Addresses:
Icli S, Ege Univ, Fac Sci, Dept Chem, TR-35100 Bornova, Izmir, Turkey
Eastern Mediterranean Univ, Dept Chem, TR-10 Mersin, Turkey
Univ Rochester, Dept Chem, Rochester, NY 14627
TUBITAK, Marmara Res Ctr, Res Inst Basic Sci, Dept Chem, TR-41470 Gebze, Turkey
Publisher:
ELSEVIER SCIENCE BV, AMSTERDAM
IDS Number:
YK855
ISSN:
0022-2313
SYNTHESIS AND PROPERTIES OF A NEW PHOTOSTABLE
POLYMER: PERYLENE-3,4,9,10-TETRACARBOXYLIC ACID BIS(N,N'-DODECYLPOLYIMIDE)
Icil H, Icli S
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
35 (11): 2137-2142 AUG 1997
Abstract:
The synthesis of perylene-3,4,9,10-tetracarboxylic acid-bis(N,N'-dodecylpolyimide) (poly
PTDI) and polyamic acid has been achieved from perylene dianhydride and dodecylamine. It
was found that this new polyimide has very high thermal photostability. Poly PTDI
decomposes at 475 °C and shows weak fluorescence compared with the monomer PTDI
possibly due to aggregration in the polymer. Its solubility in some of the common organic
solvents, acetonitrile, dimethyl formamide, etc., makes spectroscopic and photochemical
studies and applications possible in the liquid phase. The emission characteristics are similar
to mono PTDI. Poly PTDI, a luminescent electron acceptor polymer, is a new reliable probe
for a photosensitizer at energy transfer and electron transfer photochemical reactions. (C)
1997 John Wiley & Sons, Inc.
KeyWords Plus:
POLYIMIDES, DIIMIDE
Addresses:
Icil H, EASTERN MEDITERRANEAN UNIV, FAC ARTS & SCI, DEPT CHEM, POB 95,
FAMAGUSTA, N. CYPRUS,TR-10 MERSIN, TURKEY
EGE UNIV, FAC SCI, DEPT CHEM, IZMIR, TURKEY
TUBITAK, MARMARA RES CTR, RES INST BASIC SCI, DEPT CHEM, TR-41470
GEBZE, TURKEY
Publisher:
JOHN WILEY & SONS INC, NEW YORK
IDS Number:
XM222
ISSN:
0887-624X
A SINGLET OXYGEN QUENCHER IN PLANTS: VIRGATIC ACID
FROM SALVIA SPECIES
Icli S, Icil H, Sayil C
SPECTROSCOPY LETTERS
30 (4): 641-648 1997
Abstract:
Virgatic acid triterpene, extracted from salvia plants, is found to be quenched by singlet
oxygen at chemical and photosensitized oxygenations. A charge transfer energy transfer is
attributed to the quenching of singlet oxygen, which may be accounted as a protective
mechanism of salvia plants to photooxygenations.
Addresses:
Icli S, TUBITAK, MARMARA RES CTR, RES INST BASIC SCI, DEPT CHEM, POB 21,
TR-41470 GEBZE, TURKEY
EASTERN MEDITERRANEAN UNIV, FAC ARTS & SCI, DEPT CHEM, MERSIN 10,
TURKEY
EGE UNIV, FAC SCI, DEPT CHEM, TR-35100 BORNOVA, TURKEY
Publisher:
MARCEL DEKKER INC, NEW YORK
IDS Number:
XB982
ISSN:
0038-7010
A THERMAL AND PHOTOSTABLE REFERENCE PROBE FOR Qf
MEASUREMENTS: CHLOROFORM SOLUBLE PERYLENE 3,4,9,10TETRACARBOXYLIC ACID-BIS-N,N'-DODECYL DIIMIDE
Icli S, Icil H
SPECTROSCOPY LETTERS
29 (7): 1253-1257 1996
Abstract:
The synthesis of a chloroform soluble perylene 3,4,9,10-tetracarboxylic acid-bis-N,N'-dodecyl
diimide via condensation of perylene 3,4,9,10-tetracarboxylic dianhydride and 1,12-diamino
dodecane is described. The thermal analysis is shown thermal stabilities above 400 °C.
Thermal and photostable dye is measured to have a fluorescence quantum yield of unity,
Qf = 1.00, in chloroform solutions. Perylene bis-dodecyl diimide is an ideal reference probe
for fluorescence quantum yield measurements in 500-650 nm region and a reliable soluble
photosensitizer for solar photochemical applications.
Addresses:
Icli S, TUBITAK, MARMARA RES CTR, RES INST BASIC SCI, DEPT CHEM, PK 21,
TR-41470 GEBZE, TURKEY
EASTERN MEDITERRANEAN UNIV, FAC ARTS & SCI, DEPT CHEM, MERSIN 10,
TURKEY
Publisher:
MARCEL DEKKER INC, NEW YORK
IDS Number:
VK810
ISSN:
0038-7010
THE SYNTHESIS AND SPECTRAL CHARACTERISTICS OF A
SUPRAMOLECULAR MODEL - PERYLENE 3,4,9,10TETRACARBOXYLIC ACID-BIS-N,N'-p-AMINOPHENYL DIIMIDE
ICIL H, ICLI S
SPECTROSCOPY LETTERS
28 (4): 595-601 1995
Abstract:
A supramolecular structure, perylene 3,4,9,10-tetracarboxylic acid-bis-N,N'-p-aminophenyl
diimide, has high thermal and photo stabilities, detected at DSC, TGA, and emission
spectroscopy studies. The low fluorescence quantum yield of 0,20, indicates the application
possibilities on photo electron transfer reactions.
Addresses:
ICIL H, EASTERN MEDITERRANEAN UNIV, FAC SCI, DEPT CHEM, FAMAGUSTA
10, TURKEY
TUBITAK, MARMARA RES CTR, BASIC SCI RES INST, DEPT CHEM, GEBZE 41470,
TURKEY
Publisher:
MARCEL DEKKER INC, NEW YORK
IDS Number:
QZ169
ISSN:
0038-7010
THE SENSITIZED QUANTUM YIELD AT
PHOTODEHYDROGENATION REACTION OF ABIETIC ACID
ICLI S, ICIL H
SPECTROSCOPY LETTERS
28 (2): 241-248 1995
Abstract:
The re-cycled irradiation of abietic acid above 300 nm with benzophenone and copper(II)
pivalate in toluene solution has resulted in conversion to dehydroabietic acid with a quantum
yield ranging from 9.6 to 5.5. The high quantum yield may be attributed to the re-generation
of benzophenone by means of the electron transfer reaction of benzophenone radical and to
some additional reactions on formation of dehydroabietic acid.
Addresses:
ICLI S, TUBITAK, MARMARA RES CTR, BASIC SCI RES INST, DEPT CHEM PK21,
GEBZE 41470, TURKEY
EASTERN MEDITERRANEAN UNIV, FAC SCI,DEPT CHEM, MERSIN 10, TURKEY
Publisher:
MARCEL DEKKER INC, NEW YORK
IDS Number:
QL114
ISSN:
0038-7010
NMR, ABSORPTION AND FLUORESCENCE PARAMETERS OF
AZLACTONES
ICLI S, ICIL H, ALP S, KOC H, MCKILLOP A
SPECTROSCOPY LETTERS
27 (9): 1115-1128 1994
Abstract:
Absorption and fluorescence wavelenghts for a series of azlactones have been measured from
acetonitrile solutions that had no pre-light exposure. Fluorescence quantum yields, Qf, are
found to be in general less than 0.01, excluding the the derivatives with naphthyl and
p-dimethylaminophenyl substituents. Previously reported Qf values did not fit to our results.
Addresses:
ICLI S, MARMARA RES CTR, BASIC SCI RES INST, DEPT CHEM, TUBITAK,
TURKEY
AEGEAN UNIV, FAC SCI, DEPT CHEM, BORNOVA, TURKEY
UNIV E ANGLIA, SCH CHEM SCI, NORWICH NR4 7TJ, NORFOLK, ENGLAND
EASTERN MEDITERRANEAN UNIV, FAC SCI, DEPT CHEM, MERSIN 10, TURKEY
Publisher:
MARCEL DEKKER INC, NEW YORK
IDS Number:
PM820
ISSN:
0038-7010
PHOTOLYSIS OF ABIETIC ACID TO DEHYDROABIETIC ACID AND
HYDROGEN
ICLI S, ICIL H
SPECTROSCOPY LETTERS
27 (8): 1041-1048 1994
Abstract:
Abietic acid, which is the terpene acid component of natural colophony, was irradiated at
above 300 nm in the presence of benzophenone and a colloidal platinum catalyst. The
expected product of dehydroabietic acid was formed to the extent of 81 %, hydrogen
generation occurred to a negligibly small amount. The hydrogen generation, even as a byproduct of an aimed solar photochemical product, do not carry appreciable importance
because the hydrogen yield is too low to have any value on use.
Addresses:
ICLI S, MARMARA RES CTR, TUBITAK, BASIC SCI RES INST, DEPT CHEM, POB 21,
GEBZE 41470, TURKEY
EASTERN MEDITERRANEAN UNIV, FAC SCI, DEPT CHEM, MERSIN 10, TURKEY
Publisher:
MARCEL DEKKER INC, NEW YORK
IDS Number:
PG121
ISSN:
0038-7010
FLUORESCENCE QUANTUM YIELDS OF PERYLENE 3,4,9,10TETRACARBOXYLIC ACID-BIS-N,N'-ARYL(ALKYL) DIIMIDES
ICLI S, ICIL H
SPECTROSCOPY LETTERS
27 (3): 323-332 1994
Abstract:
The synthesized perylenes 3,4,9,10-tetracarboxylic acid N,N'-ethyl, phenyl, rho-anisyl, alphanaphthyl and acetyl diimides have shown great variations in absorption and emission spectra.
The variation in molar extinction coefficients and fluorescence quantum yields have indicated
that steric and electronic effects, caused by N-substitution, alters emission characteristics of
perylene diimides significantly.
KeyWords Plus:
DYES
Addresses:
ICLI S, EGE UNIV, FAC SCI, DEPT CHEM, IZMIR, TURKEY
EASTERN MEDITERRANEAN UNIV, FAC SCI, DEPT CHEM, N. CYPRUS, TURKEY
Publisher:
MARCEL DEKKER INC, NEW YORK
IDS Number:
NC844
ISSN:
0038-7010
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