New ways of functionalising BODIPY dyes and the effect on the photophysical properties

报告题目：New ways of functionalising BODIPY dyes and the effect on the photophysical properties

报告人：Prof. Dr. Wim Dehaen

Katholieke Universiteit Leuven

地点：独墅湖校区907#楼1445室

时间：2015年07月23日（星期四）下午15:00—16:00

报告摘要

BODIPY is an interesting fluorescent unit with superior properties. Several ways of functionalizing this chromophore were developed in the Leuven laboratory since 2005 and a review will be given, including some of the more recent results. Firstly, 3,5-dichloroBODIPY was readily prepared and substituted with nucleophiles. Pd-catalysed couplings (Stille, Suzuki, Heck, Sonogashira) are also possible, and intramolecular couplings to restricted dyes. We have studied the conjugation to BODIPY of ionophores for potassium, zinc, copper, and protons. The 2- and 3-monohalogenated BODIPYs can be prepared and substituted, and pyrimidinylBODIPY can be disubstituted at the at pyrimidine ring. Recent ways of functionalisation are the oxidative nucleophilic substitution of hydrogen (ONSH ), possible with N, C nucleophiles, and the vicarious nucleophilic substitution (VNS) with haloesters and haloketones, and this was extended to ethenylation (see example below). Some work involving the substitution of 8-chloroBODIPY, and our very recent work on 3,5-CH-arylation or alkylation will also be reported.

Selected recent references

V. Leen, V. Z. Gonzalez, W. De Borggraeve, N. Boens, W. Dehaen Chem. Commun. 2010, 4906-4908, S. Yin, V. Leen, S. Van Snick, N. Boens, W. Dehaen,Chem. Commun. 2010, 6329-6331; V. Leen, M. Van der Auweraer, N. Boens, W. Dehaen, Org. Lett. 2011, 13, 1470-1473; V. Leen, D. Miscoria, S. Yin, A. Filarowski, J.M. Ngongo, M. Van der Auweraer, N. Boens, W. Dehaen, J. Org. Chem. 2011, 76, 8168-8176; V. Leen, T. Leemans, N. Boens, W. Dehaen, Eur. J. Org. Chem. 2011, 4386-4396. S. Yin, V. Leen, C. Jackers, D. Beljonne, B. Van Averbeke, M. Van der Auweraer, N. Boens, W. Dehaen, Chem.-Eur. J. 2011, 17, 13247-13257; B. Verbelen, V. Leen, L. Wang, N. Boens, W. Dehaen Chem. Commun. 2012, 48, 9129-9131; N.Boens, V. Leen, W. Dehaen, Chem. Soc. Rev. 2012, 41, 1130-1172 ; N. Boens, V. Leen, W. Dehaen, L. Wang, K. Robeyns, W. Qin, X. Tang, D. Beljonne, C. Tonnelé, J. M. Paredes, M. J. Ruedas-Rama, A. Orte, L. Crovetto, E. M. Talavera, J. M. Alvarez-Pez, J. Phys. Chem. A, 2012, 116, 9621-9631. ; V. Leen, P. Yuan, L. Wang, N. Boens, W. Dehaen, , Org. Lett. 2012, 14, 6150-6153; . Wang, B. Verbelen, C. Tonnele, D. Beljonne, R. Lazzaroni, V. Leen, W. Dehaen, N. Boens Photochem. Photobiol. Sci. 2013, 12, 835-847; N. Boens, L. Wang, V. Leen, P. Yuan, B. Verbelen, W. Dehaen, M. Van der Auweraer, W. De Borggraeve, L. Van Meervelt, J. Jacobs, D. Beljonne, C. Tonnelé, R. Lazzaroni, M. J. Ruedas-Rama, A. Orte, L. Crovetto, E. M. Talavera, J. M. Alvarez-Pez, , J. Phys. Chem (A) 2014, 118, 1576-1594; A. Filarowski, M. Lopatkova, P. Lipkowski, M. Van der Auweraer, V. Leen, W. Dehaen, , J. Phys. Chem.B 2015, 119, 2576-2584;B. Verbelen, S. Boodts, J. Hofkens, N. Boens, W. Dehaen, Angew. Chem. Int. Ed. 2015, 54, 4612-4616.

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