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Review
. 2016 Oct 1;7(10):6298-6308.
doi: 10.1039/c6sc01832g. Epub 2016 Jun 27.

Click-chemistry approaches to π-conjugated polymers for organic electronics applications

Assunta Marrocchi  1 , Antonio Facchetti  2   3   4 , Daniela Lanari  5 , Stefano Santoro  1 , Luigi Vaccaro  1
Affiliations
Review

Click-chemistry approaches to π-conjugated polymers for organic electronics applications

Assunta Marrocchi et al. Chem Sci. .

Abstract

Given the wide utility of click-chemistry reactions for the preparation of simple moieties within large architecturally complex materials, this minireview article aims at surveying papers exploring their scope in the area of π-conjugated polymers for application in organic electronics to enable advanced functional properties.

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Figures

Scheme 1
Scheme 1. A general representation of polymerization using Stille, Suzuki, Heck and direct arylation cross-coupling reactions.
Scheme 2
Scheme 2. Synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition of azides and terminal alkynes.
Scheme 3
Scheme 3. Most recent CuAAC mechanism proposed by Fokin and co-workers.
Scheme 4
Scheme 4. Synthesis of “click” polymers P1–P3.
Scheme 5
Scheme 5. Synthesis of “click” polymers P4–P9.
Scheme 6
Scheme 6. Synthetic routes for the “click” polymers P10–P12.
Scheme 7
Scheme 7. Preparation of semiconducting polymer thin films via surface-initiated stepwise “click” polymerization.
Fig. 1
Fig. 1. Surface morphology imaged by contact mode AFM. (a) Topograph of the film of P13 prepared on a quartz surface (roughness, rms, ∼6 nm); (b) corresponding lateral force image. Centre area has a trench in the film made by ‘‘nanoshaving’’ to show continuity of the cylindrical domains. Reproduced with permission. Copyright 2011, The Royal Society of Chemistry.
Scheme 8
Scheme 8. Synthetic route to oligophenylenetriazoles O1 and O2. (A) CuSO4·5H2O (2 mmol%), SA (15 mmol%), EtOH/H2O (2.5 : 1), rt; (B) CuSO4·5H2O (2 mmol%), SA (15 mmol%), CH3CN/H2O (2.5 : 1), rt.
Scheme 9
Scheme 9. Synthesis of 1,4-disubstituted 1,2,3-triazoles O3 from azides 19 and corresponding terminal acetylenes.
Scheme 10
Scheme 10. Synthetic route to P14–P16. TCNE and TCNQ stand for tetracyanoethylene and 7,7,8,8-tetracyanoquinodimethane, respectively.
Fig. 2
Fig. 2. (A) Device structure and (B) representative I–V curves of the devices incorporating (a) P14, (b) P15, and (c) P16 30 nm thick films [adapted from ref. 37].
Fig. 3
Fig. 3. Schematic illustration of Jørgensen and Eichen “click” approach to oligo-arylene-vinylenes. Adapted with permission. Copyright 2011, Wiley-VCH.
Fig. 4
Fig. 4. Examples of π-conjugated “click” oligo-arylene-vinylenes reported by Jørgensen et al. and Eichen et al.
Scheme 11
Scheme 11. Reaction schematics for the molecular wires O6 and O7 self-assembled on Au surface.
Scheme 12
Scheme 12. Syntheses of poly(vinylsulfide)s P17 via thiol-yne click polymerization reactions of monomers 25 and 26.
Scheme 13
Scheme 13. Synthesis of hyperbranched π-conjugated polymer P18 by catalyst-free thiol-yne reaction between monomers 25 and 27.
None
Assunta Marrocchi
None
Antonio Facchetti
None
Daniela Lanari
None
Stefano Santoro
None
Luigi Vaccaro
See this image and copyright information in PMC

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