Backbone functionalisation of conjugated polymers is crucial to their performance in many applications, from electronic displays to nanoparticle biosensors, yet there are limited approaches to introduce functionality. To address this challenge we have developed a method for the direct modification of the aromatic backbone of a conjugated polymer, post-polymerisation. This is achieved via a quantitative nucleophilic aromatic substitution (SNAr) reaction on a range of fluorinated electron-deficient comonomers. The method allows for facile tuning of the physical and optoelectronic properties within a batch of consistent molecular weight and dispersity. It also enables the introduction of multiple different functional groups onto the polymer backbone in a controlled manner. To demonstrate the versatility of this reaction, we designed and synthesised a range of emissive poly(9,9-dioctylfluorene-alt-benzothiadiazole) (F8BT)-based polymers for the creation of mono and multifunctional semiconducting polymer nanoparticles (SPNs) capable of two orthogonal bioconjugation reactions on the same surface.
Bibliographical noteFunding Information:
M.H. acknowledges financial support from the EPSRC (grant numbers: EP/G037515/1; EP/L016702/1) and the British Council (337323). We thank CSIRO for the sponsorship of A.C., and the China Scholarship Council for S.C. M.M.S. acknowledges support from the ERC Seventh Framework Programme Consolidator grant “Naturale CG” (616417), the Wellcome Trust Senior Investigator Award (098411/Z/12/Z), the Imperial College BHF Centre for Cardiac Regeneration (RM/13/1/30157), the i-sense EPSRC IRC in Early Warning Sensing Systems for Infectious Diseases (EP/K031953/1) and the EPSRC grant "Bio-functionalised nanomaterials for ultrasensitive biosensing" (EP/K020641/1).
© 2018, The Author(s).
ASJC Scopus subject areas
- General Chemistry
- General Biochemistry, Genetics and Molecular Biology
- General Physics and Astronomy