Yi-Lin Wu

 

PhD Student

Location:

HCI G-314

Phone:

+41-44-632 2636

e-mail:

Yi-Lin Wu

Education

2002-2005:

B.S. in Chemistry, National Taiwan University, Taipei, Taiwan
Undergraduate Research with Prof. T.-Y. Luh

2005:

Visiting Student in the Hamaguchi Lab, The University of Tokyo

2007-2008:

M.Sc. in Chemistry, ETH Zürich

2008:

Master Thesis with Prof. F. Diederich, ETH Zürich

since 2008:

PhD with F. Diederich, ETH Zürich

Properties and Reactivities of Acetylenic Functionalities

The C(sp)-C(sp) triple bond has long been recognized as a useful and active structural moiety mediating intramolecular charge-transfer interaction. To explore the chemistry of such functionality, during the past few years, the Diedeich group has devoted to discover novel and stable carbon-rich materials that exhibit interesting photophysical properties and chemical reactivities.

Utilizing the diethynylethene or tetraethynylethene as building blocks, the Diederich group, in the past decades, synthesized and studied series of acetylenic marcocylces, such as perethynylated dehydroannulenes, radialenes and radiaannulenes. Based on these pioneering works, a new family of carbon marcocycles is proposed; with delicate structural design, the physical properties of the as-synthesized molecules would be studied by means of spectroscopic and computational methods to give profound understanding of the aromaticity and (cross)conjugation interaction across the C≡C, C=C and C—C backbone.

The “click-type” reaction of thermal [2+2] cycloaddition-cycloreversion between electron-rich acetylenes and cyanoethenes is recently found in our group, yielding a large variety of non-planar charge-transfer chromophores which could be potential candidates for electrochemical and NLO applications. The scope of the electrophilic components in such reaction was serendipitously found to be extended to some weaker cyanocarbons, which greatly expand the usage of this methodology fabricating charge-transfer chromophores. Also, the mechanism and application of this reaction are currently under examination.

Publications

P. D. Jarowski, Y.-L. Wu, C. Boudon, J.-P. Gisselbrecht, M. Gross, W. B. Schweizer, F. Diederich, Org. Biomol. Chem., in press. New Charge-Transfer Chromophores by Formal Cycloaddition of Donor-Substituted Alkynes to Dicyanovinyl Derivatives.

P. D. Jarowski, Y.-L. Wu, W. B. Schweizer, F. Diederich, Org. Lett. 2008, 10, 3347-3350. 1,2,3-Triazoles as Conjugative pi-Linkers in Push-Pull Chromophores: Importance of Substituent Positioning on Intramolecular Charge-Transfer.

C.-L. Lin, Y.-L. Wu, C.-L. Chen, C.-M. Chou, T.-Y. Luh, J. Org. Chem. 2007, 72, 8531-8534. Sequential Electrochemical Oxidation of Alternating Benzene-Furan Oligomers.

Last update: Jan. 2009