A side-chain engineering approach to solvent-resistant semiconducting polymer thin films

Guo, Zihao; Ai, Na; McBroom, Connor Ryan; Yuan, Tianyu; Lin, Yan‐Ru; Roders, Michael; Zhu, Congzhi; Ayzner, Alexander L.; Pei, Jian; Fang, Lei

doi:10.1039/c5py01669j

Cited by 35 publications

(43 citation statements)

References 34 publications

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“…We first performed thermogravimetric analysis (TGA) of BocPIQA to demonstrate a weight loss at 160 C-200 C ( Figure 3B), representing the Boc cleavage process. 59 This phenomenon was similar to that of BocIQA ( Figure S21), and the 22% weight loss agreed well with the theoretical weight percentage of Boc groups in BocPIQA (23%). Furthermore, FT-IR was used to characterize the chemical structure before and after the thermal cleavage.…”

Section: Synthesis and Characterizationsupporting

confidence: 84%

“…This problem can be solved by a reversible hydrogen-bond protection strategy. [55][56][57][58][59] The N-H groups in the PIQA backbone can be reversibly protected by bulky tert-butyloxycarbonyl (Boc) groups. As a result, much higher solubility of the Boc-functionalized ladder polymer (BocPIQA, Figure 1B) was expected for characterization and solution processing.…”

Section: Molecular Designmentioning

confidence: 99%

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Synthesis and Solution Processing of a Hydrogen-Bonded Ladder Polymer

Zou¹,

Ji²,

Cai³

et al. 2017

Chem

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Fang and coworkers report a conjugated ladder polymer featuring a rigid coplanar backbone and self-complementary intermolecular hydrogen bonds. The gramscale synthesis was achieved in three steps with overall 66% yield. Reversible hydrogen-bond protection and cleavage enabled solution-phase characterization of this highly insoluble polymer. Solution-processed thin films demonstrated robust resistance to aggressive solvents after simple thermal annealing. Carbonization of this fused-ring polymer leads to carbon materials with high graphitic content.

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Section: Synthesis and Characterizationsupporting

confidence: 84%

Section: Molecular Designmentioning

confidence: 99%

Synthesis and Solution Processing of a Hydrogen-Bonded Ladder Polymer

Zou¹,

Ji²,

Cai³

et al. 2017

Chem

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“…[17][18][19][20] The advantage of such design lies in the complete removal of the insulating functionalizing chains from the active layer, often resulting in improvements of charge transport properties. [16,17,[21][22][23][24][25][26] Very recently, such an approach was extended to naphthalene diimide (NDI) containing polymers, one of the most promising classes of n-type polymeric semiconductors. [27,28] In this strategy, the imide nitrogen was functionalized -either directly or through an alkyl spacer -with a cleavable ester functionality.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Naphthalene Dianhydride Bithiophene Copolymers by Direct Arylation Polycondensation and the Latent Pigment Approach

et al. 2019

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An alternating naphthalene dianhydride bithiophene copolymer (PNDAT2) is prepared by a combined direct arylation polycondensation and the latent pigment approach. PNDAT2 is the first reported example of an alternating conjugated polymer containing naphthalene dianhydride, the oxo‐analogue of naphthalene diimide often used in electron‐acceptor conjugated polymers. PNDAT2 is resistant to organic solvents and can be generated directly as film by thermal treatment of the soluble tetraester precursor PNTET2. PNDAT2 is characterized by a LUMO level of −3.9 eV, similar to that of established naphthalene diimide containing soluble copolymers. This route to insoluble electron acceptor copolymers by thermal cleavage of soluble precursors is an alternative to classical cross‐linking or orthogonal processing strategies.

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“…A different method to stabilize polymer films makes use of cleavable moieties that solubilize the polymer until removed. The cleavable chains can be designed to cleave by several external stimuli, such as heat, UV‐light, acid, or base . Many of these make use of large side chains, which means that the cleaved off groups stay in the film.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Isoindigo‐Based Polymers with Thermocleavable Side Chains

Bini

Andersson

et al. 2018

Macro Chemistry & Physics

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Stability of bulk heterojunction films for organic solar cells is a critical factor for commercial viability. One method to stabilize these films is to include cleavable side chains, which reduce the solubility of the polymers when removed. In order to study the stabilizing effect of cleavable side chains, a series of random copolymers using isoindigo with 0, 10, 20, 50, and 100% thermally cleavable side chains based on the tert‐butyloxycarbonyl (t‐BOC) group are synthesized. The polymers show a distinct one‐step thermal cleavage of the side chains, with no separable dealkylation and decarboxylation steps. The thermal stability in film is studied with transmission electron microscopy and atomic force microscopy. The polymer with all t‐BOC side chains on isoindigo significantly improves thermal stability with regard to crystal growth and phase separation in film. These results suggest BOC‐substitution can be used for large scale processing to produce insoluble polymer films with a high degree of thermal stability.

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A side-chain engineering approach to solvent-resistant semiconducting polymer thin films

Abstract: Latent H-bonds in conjugated statistical copolymers rendered semiconducting thin films resistant to solvent immersion.

Cited by 35 publications

References 34 publications

Synthesis and Solution Processing of a Hydrogen-Bonded Ladder Polymer

Synthesis and Solution Processing of a Hydrogen-Bonded Ladder Polymer

Preparation of Naphthalene Dianhydride Bithiophene Copolymers by Direct Arylation Polycondensation and the Latent Pigment Approach

Synthesis and Characterization of Isoindigo‐Based Polymers with Thermocleavable Side Chains

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