Efficient Synthesis of a Multifunctional Dye Conjugate for Photorefractive Applications

Abstract

An efficient method for the synthesis of a multifunctional dye conjugate containing an electrooptical merocyanine chromophore and a photoconducting triphenylamine electrophore is described. In the first step 4,4′-di(9-carbazolyl)-substituted 4′′-hydroxytriphenylamine 7 is reacted with 2,3-dihydro-5H-oxazolo[3,2-a]pyrid-5-one (6) by dihydrooxazole ring opening leading to precursor 8 which could be converted to the bichromophoric conjugate 2 in a Knoevenagel condensation. UV/VIS spectroscopy and cyclic voltammetry of the bichromophoric compound 2 revealed optical and electrical properties that make such multifunctional dye conjugates highly promising for photorefractive applications.

Key words

dyes - electron transfer - photorefractive - ring opening - spectroscopy

References

• 1a Moerner WE. Silence SM. Chem. Rev.  1994,  94:  127 
• 1b Zilker SJ. ChemPhysChem  2000,  1:  72 
• 1c Würthner F. Wortmann R. Meerholz K. ChemPhysChem  2002,  3:  17 
• 2a Andre B. Lever R. Moisan JY. Chem. Phys.  1989,  137:  281 
• 2b Loufty RO. Hor A.-M. Hsiao C.-K. Baranyi G. Kazmaier P. Pure Appl. Chem.  1988,  60:  1047 
• 3 Wolff JJ. Wortmann R. Adv. Phys. Org. Chem.  1999,  32:  121 
• 4a Würthner F. Wortmann R. Matschiner R. Lukaszuk K. Meerholz K. DeNardin Y. Bittner R. Bräuchle C. Sens R. Angew. Chem., Int. Ed. Engl.  1997,  36:  2865 ; Angew. Chem. 1997, 109, 2933
• 4b Würthner F. Thalacker C. Matschiner R. Lukaszuk K. Wortmann R. Chem. Commun.  1998,  1739 
• 4c Beckmann S. Etzbach K.-H. Krämer P. Lukaszuk K. Matschiner R. Schmidt AJ. Schuhmacher P. Sens R. Seybold G. Wortmann R. Würthner F. Adv. Mater.  1999,  11:  536 
• 4d Würthner F. Synthesis  1999,  2103 
• 5 Würthner F. Yao S. Schilling J. Wortmann R. Redi-Abshiro M. Mecher E. Gallego-Gomez F. Meerholz K. J. Am. Chem. Soc.  2001,  123:  2810 
• 6a Hohle C. Hofmann U. Thelakkat M. Strohriegl P. Haarer D. Zilker SJ. J. Mater. Chem.  1999,  9:  2205 
• 6b Thelakkat M. Schmitz C. Hohle C. Strohriegl P. Schmidt H.-W. Hofmann U. Schloter S. Haarer D. Phys. Chem. Chem. Phys.  1999,  1:  1693 
• 7 Tilak BD. Ayyangar NR. Rao US. Indian J. Chem., Sect. B  1984,  23B:  18 
• 8a Ambrose JF. Nelson RF. J. Electrochem. Soc.  1968,  115:  1159 
• 8b Mecher A. Bräuchle C. Hörhold HH. Hummelen JC. Meerholz K. Phys. Chem. Chem. Phys.  1999,  1:  1749 
• 9 Perrin DD. Armarego WLF. In Purification of Laboratory Chemicals   2nd ed.:  Pergamon Press; Oxford: 1980.