Band gap engineering of donor–acceptor co-crystals by complementary two-point hydrogen bonding

Yee, Nathan; Dadvand, Afshin; Perepichka, Dmitrii F.

doi:10.1039/d0qm00500b

Cited by 16 publications

(16 citation statements)

References 59 publications

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“…The close contact between donor and acceptors brought about by hydrogen bonding allowed for electron transport between them. These observations led to a series of recent publications which expanded the structural scope of both donor and acceptor moieties 55–57 . As a result of complexation between donor and acceptor small molecules, the authors observed lower band gaps, intense absorption in the near infrared region, and short inter‐chromophore separation, all of which make these molecules interesting candidates for organic transistors.…”

Section: Hydrogen Bondingmentioning

confidence: 99%

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%

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 shift depends on the nature of the metal coordinated to the organic ligand and can reach up to 1.7 V. Thus, the interaction of Lewis acid with the electron acceptor can promote redox transformations, including catalysis. Besides, the ability to control the position and nature of the frontier orbitals of organic electron acceptors can serve as a convenient tool for fine-tuning photoactive donor−acceptor systems 66 for photovoltaics, nonlinear optics, and electrochromic compounds and sensors.…”

Section: ■ Conclusionmentioning

confidence: 99%

Complexes of Metal Halides with Unreduced o-(Imino)quinones

et al. 2021

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A series of complexes of metal halides with unreduced quinone-type ligands have been synthesized and characterized in detail. The 3,6-di-tert-butyl-obenzoquinone (1) and 4,6-di-tert-butyl-N-aryl-substituted o-iminobenzoquinones (2−5) (aryl is 2,6-dimethylphenyl in 2, 2-methyl-6-ethylphenyl in 3, 2,6-diethylphenyl in 4, and 2,6-diisopropylphenyl in 5) were used to obtain the molecular complexes with metal 12 group halides as well as with indium(III) iodide. The molecular structures of five complexes, bearing an unreduced form of redox-active ligand, have been established by single-crystal X-ray analysis. The spectral data, electrochemical measurements, and DFT calculations indicate the significant transformations of the molecular orbitals of 1−5 upon complexation with Lewis acids. The reduction potentials of o-(imino)quinones in complexes with metal halides shift into the anodic region versus uncoordinated ones. The choice of metal halide allows varying the shift magnitude up to 1.7 V in 2•CdI 2 . The change of the oxidizing ability of the 1−5 upon coordination with Lewis acids enables the oxidation of mercury and ferrocene, infeasible for free ligands.

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“…22−25 For example, a singlepoint H-bonding was used to control the assembly of a TTFimidazole donor with various acceptors, where the H-bonding polarization strengthens the CT interactions, leading to a near-IR (NIR) absorption and, often, metallic conductivity in complexes with a large ΔE offset (up to 0.7 eV). 22,23 Recently, our lab reported that complementary two- 26,27 and threepoint 28−30 H-bonding can be used for a reliable coassembly of various π-electron donors and acceptors with a relatively high ΔE offset (0.8−2.5 eV). In the case of unidirectional (two-point) H-bonding we observed a strong enhancement of the D−A interactions due to H-bonding.…”

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confidence: 99%

“…In the case of unidirectional (two-point) H-bonding we observed a strong enhancement of the D−A interactions due to H-bonding. 26,27 However, not having X-ray crystallographic data for corresponding D/A cocrystals without H-bonding, the understanding of the effect of H-bond polarization on the CT interactions relied on the density functional theory (DFT) predictions and solution studies.…”

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confidence: 99%

Hydrogen Bonding Versus π-Stacking in Charge-Transfer Co-crystals

Yee

Dadvand

Hamzehpoor

et al. 2021

Crystal Growth & Design

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We report a comparative study of two structurally similar donor–acceptor complexes with (1a) and without (2a) H-bonding using X-ray crystallography, spectroscopic analysis, and density functional theory calculations. H-Bonding enhances the donor–acceptor interactions, as manifested in a narrower band gap and shorter π-stacking distance in 1a versus 2a, despite 2 being a stronger donor than 1. Thin-film transistors of 1a showed ambipolar charge transport with “double dip” characteristics, whereas no transistor behavior was observed for 2a.

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Band gap engineering of donor–acceptor co-crystals by complementary two-point hydrogen bonding

Abstract: We report a detailed investigation of a series of new charge-transfer (CT) complexes assembled via a two-point complementary hydrogen bonding (H-bonding) of diindolopyrrole (DIP) electron donors with o-quinone and diazafluorenone...

Cited by 16 publications

References 59 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

Complexes of Metal Halides with Unreduced o-(Imino)quinones

Hydrogen Bonding Versus π-Stacking in Charge-Transfer Co-crystals

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