Synthesis and optoelectronic properties of benzodithiophene-based conjugated polymers with hydrogen bonding nucleobase side chain functionality

Sabury, Sina; Adams, Tyler J.; Kocherga, Margaret; Kilbey, S. Michael; Walter, Michael G.

doi:10.1039/d0py00972e

Cited by 16 publications

(26 citation statements)

References 92 publications

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“…Reproduced with permission. 63 Copyright 2020, RSC Publishing. (B) Chemical structure and polymorphic crystal structures of ellipticine, showing unit cells (orange dash) and hydrogen bonding interactions (blue dash).…”

Section: Hydrogen Bondingmentioning

confidence: 99%

“…Analogously, nucleobases can form hydrogen bonded pairs through various carbonyl and amine acceptor/donor pairs. In 2020, Sabury et al demonstrated how hydrogen bonding between nucleobases in side‐chains of conjugated polymers direct the self‐assembly of polymer chains 63 . Adenine‐ and thymine‐functionalized conjugated polymers (Figure 3) exhibited large bathochromic shifts in solid state absorbance compared to polymers with simple alkoxy chains due to stronger polymer chain aggregation brought on by hydrogen bond facilitated phase separation and organization.…”

Section: Hydrogen Bondingmentioning

confidence: 99%

Section: Hydrogen Bondingmentioning

confidence: 99%

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Optimizing the self‐assembly of conjugated polymers and small molecules through structurally programmed non‐covalent control

Mullin

Sharber

Thomas

2021

Journal of Polymer Science

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Organic conjugated polymers and oligomers are key electronic materials for applications such as transistors, photovoltaics, and light emitting devices due to their potential for solution processability, mechanical flexibility, and precise structure-based tuning compared to inorganic materials. In dilute environments, the optoelectronic properties of conjugated polymers are largely governed by their constitutional structure and, to a lesser degree, their solution-state intramolecular configuration. In the solid state, intramolecular conformation and intermolecular electronic coupling impact these properties substantially, especially in relation to device performance. Therefore, an increasingly important area of research concerning conjugated materials is developing design strategies aimed at optimizing the solid-state packing for electronic applications. Programming solid-state packing arrangements through discrete non-covalent interactions is an emerging strategy within the context of conjugated polymers. This review focuses on the use of the two most prevalent discrete and directional interactions used to dictate the self-assembly of conjugated polymers and oligomers-hydrogen bonds and chalcogen bonds. We also discuss how these design motifs can imbue conjugated materials with appealing physical properties while simultaneously retaining or improving electronic capabilities.

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Section: Hydrogen Bondingmentioning

confidence: 99%

Section: Hydrogen Bondingmentioning

confidence: 99%

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Optimizing the self‐assembly of conjugated polymers and small molecules through structurally programmed non‐covalent control

Mullin

Sharber

Thomas

2021

Journal of Polymer Science

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“…This phenomenon results from the close arrangement and 𝜋-𝜋 interaction in conjugated structures. [53,54] The plenty of benzene rings in polymer pendent give rise to strong 𝜋-𝜋 interaction between the polymer chains, and so the polymer chains become arranged regularly during the film-forming process. The stronger optical activity for copolymer in film state is in theory desirable to realize CPL-emission.…”

Section: And Cpl Performance Of Copolymers Prepared From Hsscpmentioning

confidence: 99%

Helix‐Sense‐Selective Polymerization of Achiral Monomers for the Preparation of Chiral Helical Polyacetylenes Showing Intense CPL in Solid Film State

Yang

Zhang

et al. 2022

Macromol. Rapid Commun.

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Polymer-based circularly polarized luminescent (CPL) materials have attracted ever-increasing interest. However, to construct CPL materials from achiral monomers is still a big challenge. Here, a series of chiral helical substituted polyacetylenes are prepared by helix-sense-selective polymerization (HSSP) of achiral acetylenic monomers (achiral monomer + fluorescent monomer). HSSPs are accomplished in a bi-solvent mixture consisting of chloroform and chiral 𝜶-pinene (chiral component). Chirality transfers from the chiral component to the helical copolymers during polymerization, thereby endowing the copolymers with helical chirality. The resulting copolymers are then fabricated into blend films which exhibit intense optical activity and CPL. The monomer ratio and the physical state of the copolymers have significant impacts on their chiroptical and CPL properties. The maximum luminescence dissymmetry factor of the blend films can be up to 1.3 × 10 −2 . The universality of the established strategy for exploring polymer-based CPL materials is demonstrated by using different achiral fluorescent monomers. The present work opens a novel alternative for developing CPL-active polymeric materials starting from achiral monomers.

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“…Recently, the interaction of nucleobases molecules with carbon nanostructures and semiconductor metal oxides and their effect on the electrical conductivity were widely studied for the development of gas sensors, biosensors and optoelectronics 21 . Taking into account the side chain engineering as a method to tailor the properties of organic compound, nucleobases represent an interesting type of functionality that may be used as an order-inducing motif 22 . Very recent studies have emphasised the possibly to create new materials with complex structure and new properties based on supramolecular self-assembled nucleobase systems using DNA technology and (bio)chemistry 23 .…”

Section: Introductionmentioning

confidence: 99%

Nucleobases thin films deposited on nanostructured transparent conductive electrodes for optoelectronic applications

Breazu

Socol

Preda

et al. 2021

Sci Rep

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Environmentally-friendly bio-organic materials have become the centre of recent developments in organic electronics, while a suitable interfacial modification is a prerequisite for future applications. In the context of researches on low cost and biodegradable resource for optoelectronics applications, the influence of a 2D nanostructured transparent conductive electrode on the morphological, structural, optical and electrical properties of nucleobases (adenine, guanine, cytosine, thymine and uracil) thin films obtained by thermal evaporation was analysed. The 2D array of nanostructures has been developed in a polymeric layer on glass substrate using a high throughput and low cost technique, UV-Nanoimprint Lithography. The indium tin oxide electrode was grown on both nanostructured and flat substrate and the properties of the heterostructures built on these two types of electrodes were analysed by comparison. We report that the organic-electrode interface modification by nano-patterning affects both the optical (transmission and emission) properties by multiple reflections on the walls of nanostructures and the electrical properties by the effect on the organic/electrode contact area and charge carrier pathway through electrodes. These results encourage the potential application of the nucleobases thin films deposited on nanostructured conductive electrode in green optoelectronic devices.

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Synthesis and optoelectronic properties of benzodithiophene-based conjugated polymers with hydrogen bonding nucleobase side chain functionality

Abstract: Fundamental properties of conjugated copolymers are sensitively linked to their constitution and features of their repeat unit design that govern assembly and organization across multiple length scales, ultimately impacting device...

Cited by 16 publications

References 92 publications

Optimizing the self‐assembly of conjugated polymers and small molecules through structurally programmed non‐covalent control

Optimizing the self‐assembly of conjugated polymers and small molecules through structurally programmed non‐covalent control

Helix‐Sense‐Selective Polymerization of Achiral Monomers for the Preparation of Chiral Helical Polyacetylenes Showing Intense CPL in Solid Film State

Nucleobases thin films deposited on nanostructured transparent conductive electrodes for optoelectronic applications

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