Systematic arrangement control of functional organic molecules

Akai, Ryota; Oka, Kouki; Nishida, Ryunosuke; Tohnai, Norimitsu

doi:10.1039/d2ce00336h

Cited by 8 publications

(8 citation statements)

References 54 publications

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“…As shown in Figure S9, the UV‐vis and emission spectra of 2,6‐ADS and each organic salt in dimethyl sulfoxide (DMSO) solution were identical, indicating that the electronic structure of 2,6‐ADS remained unchanged even in the presence of amines in the solution [14e–f] . Furthermore, the 1 H NMR spectra (Figure S10) confirmed that the interaction with amine (deprotonation of the sulfo group) had no effect on the electronic structure of the anthracene moiety [14e–f] …”

Section: Resultsmentioning

confidence: 88%

Control of Relative Positions of Electron‐Donor and Electron‐Acceptor Molecules in Charge‐Transfer Complexes for Luminescent Property Modulation

Kinoshita,

Oka,

Nakajima

et al. 2023

Chemistry A European J

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Charge‐transfer complexes can exhibit various physical properties, which depend on the relative positions of electron‐donor and electron‐acceptor molecules. Several studies have investigated the relationship between the relative positions of electron‐donor and electron‐acceptor molecules and their luminescence properties. However, elucidating the pure correlation between the relative positions and detailed luminescence processes without changing their molecular structures has been unexplored. Herein, we report the relative‐position‐control based on charge‐assisted hydrogen bonds between sulfo and amino groups and on alkylamines’ steric factors, and report concomitant luminescent property modulation. From anthracene‐2,6‐disulfonic acid and 1,2,4,5‐tetracyanobenzene as electron‐donor and electron‐acceptor molecules, and various alkylamines, six charge‐transfer complexes were prepared. Different alkylamines' steric factors drastically and precisely changed the relative positions of the electron‐donor and electron‐acceptor molecules without changing their molecular structures. Consequently, the six crystals exhibited maximum emission wavelengths from 543 to 624 nm and different luminescence processes.

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Section: Resultsmentioning

confidence: 88%

Control of Relative Positions of Electron‐Donor and Electron‐Acceptor Molecules in Charge‐Transfer Complexes for Luminescent Property Modulation

Kinoshita,

Oka,

Nakajima

et al. 2023

Chemistry A European J

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“…The crystal structure for MeO-PTTP-MeO is reported here for the first time. The crystal structure for PTTP was previously obtained in ref for 213 K, but in this study, we present it for the room temperature (298 K). The crystallographic data for the two compounds are shown in Table S1 of the Supporting Information (SI).…”

Section: Resultsmentioning

confidence: 99%

Efficient Suppression of Dynamic Disorder in Organic Semiconductors via Electron-Donating and -Withdrawing Substituents

Sosorev,

Vener,

Kharlanov

et al. 2023

J. Phys. Chem. C

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Charge transport in high-mobility organic semiconductors is considerably hindered by dynamic disorder, so strategies for its suppression are in great demand. To formulate them, hidden relationships among the molecular structure, crystal structure, and dynamic disorder are to be uncovered. In this work, we show that a crossover from a layered packing into a brickwork arrangement, induced by an electron-donating substituent in the molecular structure of a conjugated oligomer, results in a significant decrease in the low-frequency Raman signal. In light of the recently suggested hypothesis about the relation between the low-frequency Raman signal and dynamic disorder, this drop is a marker of dynamic disorder suppression. Periodic (solid-state) DFT calculations confirm that the dynamic disorder decreases and reveal the suppressed contributions to it from virtually all lowfrequency vibrational modes. A similar decrease in the low-frequency Raman intensity upon electron-donating/-withdrawing substitution followed by the crossover to brickwork packing is observed in two other pairs of conjugated oligomers and a pair of annulated compounds, for which our calculations also indicate a dramatic suppression of the dynamic disorder. We anticipate that the revealed relationship among the molecular structure, crystal structure, and dynamic disorder and the suggested disorder suppression mechanism will facilitate the rational design of high-mobility organic semiconductors.

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“…Crystal engineering is the design and synthesis of molecular ordered structures based on the understanding and use of intermolecular interactions, especially hydrogen bonds and coordination bonds. [1][2][3][4][5][6] Apart from coordination bonds, the most studied nonbonding interaction in the crystal lattice is hydrogen bonding. [7][8][9][10][11][12][13][14][15] The wide exploration of hydrogen bonds has flourished owing to advances in the organic synthesis of molecules called tectonsmolecules that are designed by grafting functional groups or sticky sites by hydrogen bonds onto a central core.…”

Section: Introductionmentioning

confidence: 99%

Missing puzzle in crystal engineering: 2-pyridone and [1,3,5]-triazine-2,4-diamine, the two most common cyclic hydrogen bonding sticky sites, in a single core

et al. 2023

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Systematic arrangement control of functional organic molecules

Abstract: Functional organic molecules, especially π-conjugated molecules, have tunable functions according to their molecular design. Since their properties are significantly affected by the overlap of π-orbitals between adjacent molecules as well...

Cited by 8 publications

References 54 publications

Control of Relative Positions of Electron‐Donor and Electron‐Acceptor Molecules in Charge‐Transfer Complexes for Luminescent Property Modulation

Control of Relative Positions of Electron‐Donor and Electron‐Acceptor Molecules in Charge‐Transfer Complexes for Luminescent Property Modulation

Efficient Suppression of Dynamic Disorder in Organic Semiconductors via Electron-Donating and -Withdrawing Substituents

Missing puzzle in crystal engineering: 2-pyridone and [1,3,5]-triazine-2,4-diamine, the two most common cyclic hydrogen bonding sticky sites, in a single core

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