Post-polymerisation Functionalisation of Conjugated Polymer Backbones and Its Application in Multi-functional Emissive Nanoparticles

Overview

Journal Nat Commun

Specialty Biology

Date 2018 Aug 15

PMID 30104597

Citations 9

Authors

Adam Creamer

Christopher S Wood

Philip D Howes

Abby Casey

Shengyu Cong

Adam V Marsh

Robert Godin

Julianna Panidi

Thomas D Anthopoulos

Claire H Burgess

Tingman Wu

Zhuping Fei

Iain Hamilton

Martyn A McLachlan

Molly M Stevens

Martin Heeney

Affiliations

Soon will be listed here.

Abstract

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 (SAr) 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.

Citing Articles

Nucleophilic Aromatic Substitution of Pentafluorophenyl-Substituted Quinoline with a Functional Perylene: A Route to the Modification of Semiconducting Polymers.

Aivali S, Andrikopoulos K, Andreopoulou A Polymers (Basel). 2023; 15(12).

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Enhanced Organic Electrochemical Transistor Performance of Donor-Acceptor Conjugated Polymers Modified with Hybrid Glycol/Ionic Side Chains by Postpolymerization Modification.

Ding B, Jo I, Yu H, Kim J, Marsh A, Gutierrez-Fernandez E Chem Mater. 2023; 35(8):3290-3299.

PMID: 37123107 PMC: 10134426. DOI: 10.1021/acs.chemmater.3c00327.

Survey of Recent Advances in Molecular Fluorophores, Unconjugated Polymers, and Emerging Functional Materials Designed for Electrofluorochromic Use.

Seddiki I, NDiaye B, Skene W Molecules. 2023; 28(7).

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Modular Synthesis of Semiconducting Graft Copolymers to Achieve "Clickable" Fluorescent Nanoparticles with Long Circulation and Specific Cancer Targeting.

Creamer A, Fiego A, Agliano A, Prados-Martin L, Hogset H, Najer A Adv Mater. 2023; 36(20):e2300413.

PMID: 36905683 PMC: 7616993. DOI: 10.1002/adma.202300413.

Conformational Heterogeneity and Interchain Percolation Revealed in an Amorphous Conjugated Polymer.

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