Imperial College London


Faculty of Natural SciencesDepartment of Chemistry

Professor of Organic Materials



+44 (0)20 7594 1248m.heeney Website




401GMolecular Sciences Research HubWhite City Campus






BibTex format

author = {Rimmele, M and Ableidinger, K and Marsh, AV and Cheetham, NJ and Taublaender, MJ and Buchner, A and Prinz, J and Fröhlich, J and Unterlass, MM and Heeney, M and Glöcklhofer, F},
doi = {10.26434/chemrxiv.7265174},
publisher = {American Chemical Society (ACS)},
title = {Thioalkyl- and Sulfone-Substituted Poly(p-Phenylene Vinylene)s},
url = {},
year = {2018}

RIS format (EndNote, RefMan)

AB - <jats:p>Poly(p-phenylene vinylene)s (PPVs) have been studied for decades, but research on this interesting class of conjugated polymers is far from being completed. New applications like in bioimaging keep emerging and even simple structural variations are still waiting to be explored. Surprisingly, not even dithioalkyl-substituted PPVs (S-PPVs) have been reported in the peer-reviewed literature, although the corresponding dialkoxy-substituted PPVs (O-PPVs) like MEH-PPV or MDMO-PPV are most frequently used and although thioalkyl substituents can improve the material properties significantly. We herein report the development of a highly efficient, scalable two-step synthesis of Gilch monomers for S-PPVs starting from low-cost 1,4-diiodobenzene. A low-temperature polymerization protocol has been developed for these monomers, affording high-molecular weight S-PPVs in excellent yields. The thermal, electrochemical, and photophysical properties of S-PPVs are reported to highlight the potential of these polymers. Furthermore, treatment with dimethyldioxirane is demonstrated to result in rapid conversion into sulfone-substituted PPVs (SO<sub>2</sub>-PPVs), introducing a route to high-molecular weight SO<sub>2</sub>-PPVs with exceptional stability and solid-state photoluminescence quantum yields of up to 0.46.</jats:p>
AU - Rimmele,M
AU - Ableidinger,K
AU - Marsh,AV
AU - Cheetham,NJ
AU - Taublaender,MJ
AU - Buchner,A
AU - Prinz,J
AU - Fröhlich,J
AU - Unterlass,MM
AU - Heeney,M
AU - Glöcklhofer,F
DO - 10.26434/chemrxiv.7265174
PB - American Chemical Society (ACS)
PY - 2018///
TI - Thioalkyl- and Sulfone-Substituted Poly(p-Phenylene Vinylene)s
UR -
ER -