Summary.
A new fluorescent and photoreactive polymer, poly-(endo,exo-bis(4-(4-(diphenylamino)benzoyloxy)benzyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate), was prepared by ring opening metathesis polymerization. This polymer combines the photoreactivity of aryl esters with the fluorescence properties of derivatives of 4-(diphenylamino)benzoic acid. The polymer exhibits blue photo- and electroluminescence and can be used as active layer in organic light emitting devices (OLED). Upon irradiation with UV light (254 nm) the aromatic ester groups undergo decarboxylation, which is accompanied by the loss of photoluminescence. Photolithographic patterning of the polymer surface was used to obtain structured fluorescent surfaces and patterned OLEDs.
Similar content being viewed by others
References
C Preininger U Sauer W Kern J Dayteg (2004) Anal Chem 76 6130 Occurrence Handle10.1021/ac0499468 Occurrence Handle1:CAS:528:DC%2BD2cXnsV2it70%3D
G Kranzelbinder E Toussaere J Zyss T Kavc G Langer W Kern (2003) Appl Phys Lett 82 2203 Occurrence Handle10.1063/1.1559952 Occurrence Handle1:CAS:528:DC%2BD3sXis1OlsL0%3D
T Kavc G Langer W Kern G Kranzelbinder E Toussaere GA Turnbull IDW Samuel KF Iskra T Neger A Pogantsch (2004) Chem Mater 14 4178 Occurrence Handle10.1021/cm021148f
T Kavc G Langer P Polt K Reichmann W Kern (2002) Macromol Chem Phys 203 1099 Occurrence Handle10.1002/1521-3935(20020501)203:8<1099::AID-MACP1099>3.0.CO;2-M Occurrence Handle1:CAS:528:DC%2BD38XltVygtb0%3D
G Langer T Kavc W Kern G Kranzelbinder E Toussaere (2001) Macromol Chem Phys 202 3459 Occurrence Handle10.1002/1521-3935(20011201)202:18<3459::AID-MACP3459>3.0.CO;2-Y Occurrence Handle1:CAS:528:DC%2BD38XoslynsQ%3D%3D
MR Weinberger G Langer A Pogantsch A Haase E Zojer W Kern (2004) Adv Mater 16 30 Occurrence Handle10.1002/adma.200305681
W Schofberger N Zaami KA Mahler G Langer G Jakopic A Pogantsch W Kern F Stelzer (2003) Macromol Chem Phys 204 779 Occurrence Handle10.1002/macp.200390063 Occurrence Handle1:CAS:528:DC%2BD3sXjslOks7g%3D
T Höfler T Grießer X Gstrein G Trimmel G Jakopic W Kern (2007) Polymer 48 1930 Occurrence Handle10.1016/j.polymer.2007.01.041
Anderson JC, Reese CB (1960) Proc Chem Soc 217
D Bellus P Hrdlovic (1967) Chem Rev 67 599 Occurrence Handle10.1021/cr60250a001 Occurrence Handle1:CAS:528:DyaF1cXmvVSqtw%3D%3D
CE Kalmus DM Hercules (1974) J Am Chem Soc 96 449 Occurrence Handle10.1021/ja00809a021 Occurrence Handle1:CAS:528:DyaE2cXotFOitw%3D%3D
MA Miranda F Galindo (2004) Photo-Fries Reaction and Related Processes WM Horspool (Eds) CRC Handbook of Organic Photochemistry and Photobiology EditionNumber2 CRC Press Boca Raton
J Kopezky (1992) Photochemistry, a visual approach, chapter 10 VCH New York
RA Finnegan D Knutson (1968) Tetrahedron Lett 9 3429 Occurrence Handle10.1016/S0040-4039(00)89510-6
G Weiqiang DJ Abdallah RG Weiss (2001) J Photochem Photobiol A: Chem 139 79 Occurrence Handle10.1016/S1010-6030(00)00411-1
Z Chen Z Zhang T Zhao F Bai Y Zhang Z Wang (2001) Spectrochim Acta A 57 419 Occurrence Handle10.1016/S1386-1425(00)00350-4 Occurrence Handle1:STN:280:DC%2BD3M3gvFSrtg%3D%3D
a) Bellmann E, Shaheen SE, Thayumanavan S, Barlow S, Grubbs RH, Marder SR, Kippelen B, Peyghambarian (1998) Chem Mater 10: 1668; b) Nomura M, Fukukawa K, Shibasaki Y, Ueda M (2002) Synth Met 132: 9; c) Stampor W, Mroz W (2007) Chem Phys 331: 261
M Behl R Zentel DJ Broer (2004) Macromol Rapid Commun 25 1765 Occurrence Handle10.1002/marc.200400321 Occurrence Handle1:CAS:528:DC%2BD2cXpvV2hu7s%3D
C Slugovc (2004) Macrom Rapid Commun 25 1283 Occurrence Handle10.1002/marc.200400150 Occurrence Handle1:CAS:528:DC%2BD2cXmsFersro%3D
JA Love JP Morgan TM Trnka RH Grubbs (2002) Angew Chem Int Edit 41 4035 Occurrence Handle10.1002/1521-3773(20021104)41:21<4035::AID-ANIE4035>3.0.CO;2-I Occurrence Handle1:CAS:528:DC%2BD38XptVyhtLc%3D
Spectral database of organic compounds, National Institute of Advanced Industrial Science and Technology (2007) SDBS No 7164 (http://www.aist.go.jp/RIODB/SDBS/cgi-bin/cre_index.cgi)
MS Sanford JA Love RH Grubbs (2001) Organometallics 20 5314 Occurrence Handle10.1021/om010599r Occurrence Handle1:CAS:528:DC%2BD3MXnvFyrt7o%3D
HE Gottlieb V Kotylar A Nudelman (1997) J Org Chem 62 7512 Occurrence Handle10.1021/jo971176v Occurrence Handle1:CAS:528:DyaK2sXmvVClsbo%3D
Hattori T, Satoh T, Miyano S (1996) Synthesis 514
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Griesser, T., Rath, T., Stecher, H. et al. Photoreactive Polynorbornene Bearing 4-(Diphenylamino)benzoate Groups: Synthesis and Application in Electroluminescent Devices. Monatsh. Chem. 138, 269–276 (2007). https://doi.org/10.1007/s00706-007-0613-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-007-0613-6