S1
Supporting Information to
Synthesis of oligoarylacetylenes with defined conjugated sequences
using tailor-made soluble polymer supports
Roza Szweda,
a
Christophe Chendo,
b
Laurence Charles,
b
Paul N. W. Baxter,
a
* and Jean-François Lutz
a
*
a
Université de Strasbourg, CNRS, Institut Charles Sadron UPR22, 23 rue du Loess, 67034 Strasbourg Cedex 2,
France. Email: baxter@unistra.fr, jflutz@unistra.fr.
b
Aix Marseille Univ, CNRS, Institut de Chimie Radicalaire, Marseille, France.
Contents
A. Materials ........................................................................................................................................ S2
B. Experimental Procedures ............................................................................................................... S2
B.1. Synthesis of the polystyrene soluble supports ....................................................................... S2
B.1.1. ATRP of styrene. ........................................................................................................... S2
B.1.2. Debromination ............................................................................................................... S3
B.1.3. TMS removal ................................................................................................................. S3
B.2. Stepwise synthesis of oligoarylacetylenes............................................................................. S3
B.2.4. General procedure for the Sonogashira coupling step ................................................... S3
B.2.5. General procedure for the protodesilylation step .......................................................... S4
B.2.6. Cleavage of the oligomers ............................................................................................. S4
C. Measurements and Analysis .......................................................................................................... S5
C.3. Nuclear Magnetic Resonance (NMR) ................................................................................... S5
C.4. Size Exclusion Chromatography (SEC) ................................................................................ S5
C.5. Fourier Transform Infrared Spectroscopy (FTIR) ................................................................. S5
C.6. UV-vis Spectroscopy ............................................................................................................. S5
C.7. Fluorescence Spectroscopy ................................................................................................... S5
C.8. Matrix-Assisted Laser Desorption/Ionization MALDI ......................................................... S5
C.9. Electrospray Ionization Mass Spectrometry (ESI-MS) ......................................................... S6
D. Additional Tables and Figures....................................................................................................... S7
E. References ................................................................................................................................... S23
Electronic Supplementary Material (ESI) for Chemical Communications.
This journal is © The Royal Society of Chemistry 2017