Summary.
Among the most promising fluorescent materials for sensor applications, anthracene and its derivatives have been widely studied. In this contribution, the synthesis and characterization of a series of isomers of bis(hydroxyphenyl)anthracene derivatives are described. The preparation of the corresponding derivatives via Suzuki cross-coupling reactions is presented with particular emphasis on finding appropriate protecting groups and studying the influence of the position of the hydroxy group on the outcome of the reaction. Moreover, the effects of protonation and deprotonation on absorption and emission spectra are reported and correlated to semi-empirical quantum mechanical calculations.
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References
For examples see: a) de Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP, Rademacher JT, Rice TE (1997) Chem Rev 97: 1515; b) Balzani V, Credi A, Raymo FM, Stoddart JF (2000) Angew Chem Int Ed 39: 3348; c) Charier S, Ruel O, Baudin J-B, Alcor D, Allemand J-F, Meglio A, Jullien L, Valeur B (2006) Chem Eur J 12: 1097
a) Mancin F, Rampazzo E, Tecilla P, Tonellato U (2006) Chem Eur J 12: 1844; b) Wang Z, Zheng G, Lu P (2005) Org Lett 7: 3669
MHV Werts S Gmouh O Mongin T Pons M Blanchard-Desce (2004) J Am Chem Soc 126 16294 Occurrence Handle15600310 Occurrence Handle10.1021/ja0446606 Occurrence Handle1:CAS:528:DC%2BD2cXhtVSmtL3P
a) Yang WJ, Kim DY, Jeong M-Y, Kim HM, Lee YK, Fang X, Jeon S-J, Cho BR (2005) Chem Eur J 11: 4191; b) Kim Y-H, Jeong H-C, Kim S-H, Yang K, Kwon S-K (2005) Adv Funct Mater 15: 1799
J-P Desvergne N Lahrahar M Gotta Y Zimmermann H Bouas-Laurent (2005) J Mater Chem 15 2873 Occurrence Handle10.1039/b501093b Occurrence Handle1:CAS:528:DC%2BD2MXmtVWqsbY%3D
N Basaric P Wan (2006) J Org Chem 71 2677 Occurrence Handle16555820 Occurrence Handle10.1021/jo0524728 Occurrence Handle1:CAS:528:DC%2BD28XitVygtLk%3D
Suzuki A (2005) Chem Commun 4759
a) Chung S-J, Kim K-K, Jin J-I (1999) Polymer 40: 1943; b) Kotha S, Ghosh AK, Deodhar KD (2004) Synthesis 549; c) Kotha S, Ghosh AK (2002) Synlett 451; d) Wagner G, Herrmann R, Scherer W (1996) J Organomet Chem 516: 225; e) Hu D, Fuh RA, Li J, Corkan A, Lindsey JS (1998) Photochem Photobiol 68: 141
a) Sharma SK, Kanamathareddy S, Gutsche CD (1997) Synthesis 11: 1268; b) Geng Y, Trajkovska A, Katsis D, Ou JJ, Culligan SW, Chen SH (2002) J Am Chem Soc 124: 8337; c) Kim J, Kim YK, Park N, Hahn JH, Ahn KH (2005) J Org Chem 70: 7087; d) Gimeno N, Ros MB, Serrano JL, de la Fuente MR (2004) Angew Chem Int Ed 43: 5235
a) Tao B, Boykin DW (2004) J Org Chem 69: 4330; b) Kappaun S, Zelzer M, Bartl K, Saf R, Stelzer F, Slugovc C (2006) J Polym Sci Part A Polym Chem 44: 2130; c) Kappaun S, Sovic T, Stelzer F, Pogantsch A, Zojer E, Slugovc C (2006) Org Biomol Chem 4: 1503
PJ Kocienski (1994) Protecting Groups Georg Thieme Verlag Stuttgart
B Loev CR Dawson (1956) J Am Chem Soc 78 6095 Occurrence Handle10.1021/ja01604a039 Occurrence Handle1:CAS:528:DyaG2sXht1KjtQ%3D%3D
Vankar YD, Rao CT (1985) J Chem Research (S): 232
For examples see: a) Bandgar BP, Bettigeri SV, Phopase J (2004) Org Lett 6: 2105; b) Edsall RJJ, Harris HA, Manas ES, Mewshaw RE (2003) Bioorg Med Chem 11: 3457
M Prieto E Zurita E Rosa L Munoz P Lloyd-Williams E Giralt (2004) J Org Chem 69 6812 Occurrence Handle15387606 Occurrence Handle10.1021/jo0491612 Occurrence Handle1:CAS:528:DC%2BD2cXntVOrtLo%3D
H Beyer W Walter (1998) Lehrbuch der Organischen Chemie S. Hirzel Verlag Stuttgart
a) Kwon SK, Kim YH, Shin SC (2002) Bull Korean Chem Soc 23: 17; b) Stoessel P, Breuning E, Vestweber H, Heil H (2006) PCT Int Appl, WO 2006048268 A1
a) Valeur B (2001) Molecular Fluorescence – Principles and Applications, Wiley-VCH, Weinheim; b) Lakowicz JR (1999) Principles of Fluorescence Spectroscopy, Kluwer Academic/Plenum Publishers, New York; c) Morris JV, Mahaney MA, Huber JR (1976) J Phys Chem 80: 969; d) Kim Y-H, Kwon S-K (2006) J Appl Polym Sci 100: 2151
A Tautges (2002) J Phys Chem Lab 4 8
Here we follow the definition given in Romaner L, Heimel G, Wiesenhofer H, Scandiucci de Freitas P, Scherf U, Brédas JL, Zojer E, List EJW (2004) Chem Mater 16: 4667 rather than applying the symmetrized version we used in previous works
HE Gottlieb V Kotylar A Nudelman (1997) J Org Chem 62 7512 Occurrence Handle11671879 Occurrence Handle10.1021/jo971176v Occurrence Handle1:CAS:528:DyaK2sXmvVClsbo%3D
MJS Dewar EG Zoebisch EF Healy JJP Stewart (1985) J Am Chem Soc 107 3902 Occurrence Handle10.1021/ja00299a024 Occurrence Handle1:CAS:528:DyaL2MXktFWlsLk%3D
Ampac 5.0 User’s Manual (1994) Copyright Semichem, 7128 Summit, Shwanee, KS 66216
a) Pople JA, Beveridge DL, Dobosh PA (1967) J Chem Phys 47: 2026; b) Ridley J, Zerner M (1973) Theoret Chim Acta 32: 111
Gaussian 98, Revision A.9, Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (1998) Gaussian Inc., Pittsburgh PA
Zoa v2.0, Calbert JP, Service de Chimie des Matériaux Nouveaux, Mons (Belgium), options 3D and not antisymmetrized
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Zelzer, M., Kappaun, S., Zojer, E. et al. Synthesis and Photo Physical Properties of 9,10-Bis(hydroxyphenyl)anthracene Derivatives. Monatsh. Chem. 138, 453–464 (2007). https://doi.org/10.1007/s00706-007-0625-2
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DOI: https://doi.org/10.1007/s00706-007-0625-2