Mechanochemical Suzuki polymerization for the synthesis of polyfluorenes

ABSTRACT

Herein are reported the syntheses of poly(9,9-di-n-octylfluorenyl-2,7-diyl) (PF), poly(9,9-dioctylfluorene-alt-benzothiadiazole) (PFBT), and poly[(9,9-bis(3′-(N,N-dimethylamino)propyl)-2,7-fluorene)-alt-2,7-(9,9-dioctylfluorene)] (PFN) by employing catalytic mechanochemical Suzuki polymerization in a ball mill. This mechanochemical synthesis technique can yield soluble functionalized polyfluorenes and its derivatives in 30 min or less. Furthermore, the polymer light emitting diode and photovoltaic interfacial electrolyte, poly(9,9-bis(3′-(N,N-dimethyl)-N-ethylammoinium-propyl-2,7-fluorene)-alt-2,7-(9,9-dioctylfluprene))dibromide (PFN-Br), was obtained via a facile mechanochemical quaternization reaction at the terminal amino groups of PFN.

GRAPHICAL ABSTRACT

KEYWORDS:

• Polyfluorenes
• mechanochemistry
• Suzuki polymerization
• high speed ball milling

Acknowledgements

Dr. Nelson gratefully acknowledges the Sloan Scholars Mentoring Network of the Social Science Research Council with funds provided by the Alfred P. Sloan Foundation. The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript.

Data availability statement

NMR, UV-vis absorption and emission spectra for PF, PFBT, PFN and PFN-Br are available in supplementary information. GPC traces for PF, PFBT, and PFN and The EcoScale calculations are also available.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was supported by Alfred P. Sloan Foundation.