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Bohm, A. Arms, H. Henning, G. Blaschka, P. (BASF) German Patent, No. DE 19547209AI

The document discusses the bromination of perylene dianhydride at the 1- and 7-positions, yielding 89%. MALDI-TOF mass spectra provided evidence for the structures. Reaction temperatures of 160-180°C and solvents like quinoline or molten imidazole are needed for less reactive aromatic amines. FT-IR spectroscopy showed bands corresponding to siloxane and imide functional groups. 13C NMR showed resonances for isobutyl and propyl carbons.

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127 views2 pages

Bohm, A. Arms, H. Henning, G. Blaschka, P. (BASF) German Patent, No. DE 19547209AI

The document discusses the bromination of perylene dianhydride at the 1- and 7-positions, yielding 89%. MALDI-TOF mass spectra provided evidence for the structures. Reaction temperatures of 160-180°C and solvents like quinoline or molten imidazole are needed for less reactive aromatic amines. FT-IR spectroscopy showed bands corresponding to siloxane and imide functional groups. 13C NMR showed resonances for isobutyl and propyl carbons.

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Lodrick Wangatia
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Commercially available perylene dianhydride (PDA, 5) was brominated at the 1- and 7-positions of the molecule according to the literature

procedures20 yield 89% The matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectra provided a direct evidence for the structures of 1-3 showing a singly charged molecular ion peak, respectively, that matches the calculated value for the molecular weight of each compound
(20) Bohm, A.; Arms, H.; Henning, G.; Blaschka, P. (BASF) German Patent, No. DE 19547209AI.

Reaction temperatures between 160 and 180 _C and solvents such as quinoline or molten imidazole are necessary in the case of using less reactive aromatic amines. CV The first reduction potential (Ered) of the unsubstituted PDI reference was recorded at -600 mV versus the saturated calomel electrode (SCE), PDI(Py)2 displays an anodic shift very close to 280 mV for the first reduction potential (Ered ) -880 mV; In addition, the PDI(Py)2 dye undergoes one-electron oxidation at 590 and 760 mV as an anticipated consequence of baysubstitution of electron-donating amino groups.14
(14) Shin, W. S.; Jeong, H.-H.; Kim, M.-K.; Jin, S.-H.; Kim, M.-R.; Lee, J.-K.; Lee, J. W.; Gal, Y.-S. J. Mater. Chem. 2006, 16, 384390.

FT-IR The presence of the siloxane unit was proven by the bands at 1255 (SieCH3), 1052 (SiOSi) and 794 cm_1 (SieCH3) FTIR spectra of the resulting POSS imides exhibited a band at approximately 1465 cm_1 for the mono- and bis-POSS derivatives, assigned to the stretching mode of the CeN bond in the imide functionality [40,41].
[40] Luo Y, Lin J, Duan H, Zhang J, Lin C. Self-directed assembly of photoactive perylenediimide-bridged silsesquioxane into a superlong tubular structure. Chem Mater 2005;17(9):2234e6. [41] Icil H, Arslan E. Synthesis and spectroscopic properties of highly pure perylene fluorescent dyes. Spec Lett 2001;34(3):355e63.

13CNMR 13C NMR exhibited resonances of the isobutyl carbons at wd 24.00, 25.80 and 27.20 ppm, with resonances of the propyl carbons apparent at d 9.40e9.80 (SiCH2), 21.50-22.70 (CH2) and 40.70-44.90 ppm (CH2N). Imidization Thermal condensation of mono-amino POSS with a range of mono- and bis-anhydrides, including phthalic, perylene, naphthalene and biphenyl have recently been reported [35],
[35] Jegenathan SG, Suruliappa G, Bramer D, Kote R, Maladkar GJ. In: Corporation CSC, editor. Novel polyhedral oligomeric silsesquioxane (POSS) based fluorescent colourants; 2008. US 2008/0029739.

From thesis for mono PDI N-Cyclohexyl-1,7-dipyrrolidinylperylene-3,4:9,10-tetracarboxylic acid-3,4-anhydride-9,10-imide (6): A mixture of 50.0 mg (0.072 mmol) of 4a, 200 mg (3.60 mmol) of KOH, 0.5 mL of water and 3 mL of i-PrOH was brought to reflux. The mixture was stirred for 2.75 h and poured under stirring into 10 mL of AcOH. The resulting green precipitate was extracted with methylene chloride, washed with water, dried over MgSO4, and concentrated by rotary evaporation. Column chromatography on silica gel (chloroform/acetone/hexane (10/1/9, v/v/v)) afforded 28 mg of the starting material 4a and 17 mg (88%) of 6.

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