Polarity change of OFETs based on Dithienocoronene Diimide (DTCDI)-Derived isomeric triads end-capped with Azulene

Ran, Huijuan; Li, Fēi; Zheng, Ruisheng; Zhang, Hailu; Xie, Fuli; Jin, Pengcheng; Zheng, Lei; Wang, Xiao-Tian; Hu, Jian‐Yong

doi:10.1016/j.dyepig.2022.110311

Cited by 7 publications

(8 citation statements)

References 45 publications

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“…Therefore, linkage at the 2- or 6-positions of azulene can stabilize the LUMO level. Moreover, azulene is a 10π-electron ambipolar unit, with polarized five- and seven-membered rings, and linkage at the 6-position (on the seven-membered ring) has been reported to result in a lower LUMO level than the linkage at the 2-position (on the five-membered ring). ,,− The LUMOs of the 6,6′-BAzTDA and 2,2′-BAzTDA molecules were distributed over the entire molecules owing to the large LUMO coefficient. In addition, 6,6′-BAzTDA had a lower LUMO level than 2,2′-BAzTDA at −3.18 eV, which is conducive to n-type (electron transport) behavior.…”

Section: Resultsmentioning

confidence: 99%

“…Yamashita and colleagues − reported end-capped n-type semiconductor materials comprising trifluoromethylphenyl groups and heteroaromatic acceptors. There are also several reports of azulene end-capped materials with a large central core unit. − However, the crystal structures of most of these molecules are predominantly based on π-stacking interactions, which are influenced by terminal electron-withdrawing groups or large acceptor core units.…”

Section: Introductionmentioning

confidence: 99%

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Azulene End-Capped 1,3,4-Thiadiazole as an n-Type Organic Semiconductor with a Herringbone–Brickwork Cooperative 2D Layered Structure

Shibuya

Matsunaga

Kumaki

et al. 2022

Crystal Growth & Design

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Aromatic oligomers were synthesized by end-capping a strong acceptor unit (1,3,4-thiadiazole (TDA)) with the 2-or 6-position of azulene. The 6-azulene end-capped molecule exhibited n-type field effect transistor (FET) characteristics owing to its low lowest unoccupied molecular orbital (LUMO) energy level and layered structure stabilized by herringbone packing between the terminal azulenes and brickwork packing between the central TDA units, which resulted in high transfer integrals with low anisotropy suitable for two-dimensional (2D) charge transport. Drop-cast thin films of 6-azulene end-capped TDA had an end-on molecular orientation and in-plane 2D structure, in good agreement with the single-crystal structure. In contrast, the 2-azulene endcapped molecule exhibited slightly higher LUMO levels, slip-stacked herringbone structures, and highly anisotropic transfer integrals; therefore, it did not exhibit FET properties and had a less ordered thin-film structure. These results suggest that the azulene backbone is advantageous for the formation of herringbone structures, that torsion between aromatic units contributes to the stabilization of 2D layered structures, and that controlling crystal growth along the molecular long axis is important for the formation of oriented thin films. The structural features of the azulene-driven herringbone−brickwork cooperative structure provide a novel avenue for the molecular design of n-type semiconductor materials.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Azulene End-Capped 1,3,4-Thiadiazole as an n-Type Organic Semiconductor with a Herringbone–Brickwork Cooperative 2D Layered Structure

Shibuya

Matsunaga

Kumaki

et al. 2022

Crystal Growth & Design

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“…This nature of the transition violates the Kasha's rule [4]. The reason for this anomalous fluorescent nature is that the energy gap between the S 1 and S 2 states is relatively large (ΔE is more than 10000 cm-1), which leads to a decrease in the transition rate from S 2 to S 1 , as a result of which the radiation from S 2 to S 0 becomes dominant [10].…”

Section: Introductionmentioning

confidence: 92%

Synthesis of Push-Pull Azulene-Based Compounds

Merkhatuly¹,

Iskanderov²,

Abeuova³

et al. 2023

Eurasian J. Chem.

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Nowadays, non-benzenoid aromatic hydrocarbons are widely used as synthons for the production of new or-ganic semiconductors with interesting photophysical characteristics. For instance, a non-benzoid azulene hy-drocarbon with a polar structure, a narrow energy gap between the highest free and lowest occupied molecu-lar orbital and the ability to form stable ions can be intended as a structural moiety for the synthesis of new conjugated compounds with important optical and electronic properties. The article discusses the synthesis and investigation of the optical properties of new push-pull azulene-based compounds. It shows that Friedel-Crafts acylation is used as the key reaction for the synthesis of methyl- and phenyl-dicyanovinylated azulenes. The interaction proceeds regioselectively at the C1 and C3 positions of the five-membered azulene ring. It is identified that the synthesis of push-pull dicyanovinylated azulenes by Knoevenagel condensation of azulenyl ketones with malononitrile proceeds easily in Py and DMSO. The UF-vis spectra of the obtained azulene push-pull compounds demonstrated strong electron absorption in the visible zone with λmax at 410, 430, 434 and 452 nm associated with transport of charge between the donor azulene ring and the acceptor dicyanovinyl group. The scheme of resonant structures shows the mechanism of intramolecular donor-acceptor interaction. The structure of the synthesized push-pull dicyanovinylated nonazulenes was elucidated using modern physicochemical and spectroscopic research methods.

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“…1a). 19 These unique properties endow azulene with great promise for developing advanced materials in organic semiconductors, 20 photoswitches, 21 nonlinear optical materials, 22 chemical sensing, bioimaging, 23 and nonplanar polycyclic aromatic hydrocarbons. 24 However, investigations associated with nonalternant aromatic all-carbon nanohoops with pH reversible stimuli-responsiveness remained largely unexplored to date because of the lack of suitable stimuli-responsive all-carbon building blocks.…”

Section: Introductionmentioning

confidence: 99%

A nonalternant azulene-embedded carbon nanohoop featuring anti-Kasha emission and tunable properties upon pH stimuli-responsiveness

Jia

Wang

et al. 2023

J. Mater. Chem. C

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Polarity change of OFETs based on Dithienocoronene Diimide (DTCDI)-Derived isomeric triads end-capped with Azulene

Cited by 7 publications

References 45 publications

Azulene End-Capped 1,3,4-Thiadiazole as an n-Type Organic Semiconductor with a Herringbone–Brickwork Cooperative 2D Layered Structure

Azulene End-Capped 1,3,4-Thiadiazole as an n-Type Organic Semiconductor with a Herringbone–Brickwork Cooperative 2D Layered Structure

Synthesis of Push-Pull Azulene-Based Compounds

A nonalternant azulene-embedded carbon nanohoop featuring anti-Kasha emission and tunable properties upon pH stimuli-responsiveness

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