Contorted tetrabenzoacenes of varied conjugation: charge transport study with single-crystal field-effect transistors

Huang, Ding‐Chi; Kuo, Chih‐Yu; Ho, Man-Tzu; Lin, Bin; Peng, Wei-Tao; Chao, Ito; Hsu, Chao‐Ping; Tao, Yazhong

doi:10.1039/c7tc02254a

Cited by 21 publications

(12 citation statements)

References 61 publications

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“…Chemical Structures of Synthesized HBCs Scheme 1. Preparation of 3, 10,15,d,g,j,m,p] respect to the other two benzenes (fused at g-and p-positions), presumably due to the electronic and steric effects exerted by different functional groups.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Polysubstituted Hexa-cata-hexabenzocoronenes: Syntheses, Characterization, and Their Potential as Semiconducting Materials in Transistor Applications

Kumar¹,

Pola²,

Huang³

et al. 2019

J. Org. Chem.

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A series of tetra- and octa-substituted hexa-cata-hexabenzocoronenes (cata-HBCs) were synthesized from tetraryl olefins via iodine- and iron chloride-catalyzed oxidative cyclodehydrogenation reactions. The substitutions on the periphery of the parent HBC serve to modify the photophysical properties, highest occupied molecular orbital–lowest unoccupied molecular orbital gaps, and thermal stabilities of the respective derivatives. The crystal structures were determined to display multiple twists in the framework, resulting in different packing motifs depending on the position, type, and number of functional groups on the hexabenzocoronene framework. Nearly perfect co-facial packing to marginally or extensively shifted co-facial stacks were obtained due to substitution. The single crystals of parent HBC were used to fabricate single-crystal field-effect transistors, from which the highest p-channel mobility of 0.51 cm2 V–1 s–1 was measured. Thin-film transistors of selected HBCs were also prepared, and 0.61 cm2 V–1 s–1 was obtained for MeHBC-2. These results attest the potential of these materials as semiconducting materials.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Polysubstituted Hexa-cata-hexabenzocoronenes: Syntheses, Characterization, and Their Potential as Semiconducting Materials in Transistor Applications

Kumar¹,

Pola²,

Huang³

et al. 2019

J. Org. Chem.

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“…() In a recent experimental investigation, Huang et al reported the synthesis and charge transport properties of a series of contorted and polyfused aromatic tetrabenzoacenes and measured mobility up to 0.81 cm 2 V −1 s −1 . () Similarly, McGarry et al showed the ambipolar behavior of rubrene‐based single‐crystal OSC with hole (electron) mobility of the order of 1.54 (0.28) cm 2 V −1 s −1 . () In addition, an exhaustive study of charge transport in heterocyclic aromatic compounds were performed by Bredas and coworkers.…”

Section: Introductionmentioning

confidence: 86%

Anisotropic charge transport properties of chrysene derivatives as organic semiconductor: A computational study

Khatua

Sahoo

Sharma

et al. 2018

J of Physical Organic Chem

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We used density functional theory to calculate the angular resolution anisotropic charge mobility of the substituted chrysene molecules, viz, 4,10-diphenoxychrysene (DPC), 4,10-bis(phenylsulfanyl)chrysene (BPSC), and ethyl 8,9,12-trimethoxychrysene-6-carboxylate (ETCC). The highest occupied molecular orbital-lowest unoccupied molecular orbital gap for DPC, BPSC, and ETCC was calculated to be 3.92, 3.83, and 3.81 eV, respectively, which inferred the compounds to be wide-band-gap semiconductors indicating that the compounds should have high stability in atmospheric conditions. The fact is also supported by electronic band-structure calculation. In addition, higher electron affinity of studied compounds as compared with the bare chrysene molecule imparts enhancement of n-type character in the compounds. The maximum hole ( h Φ ) and electron mobilities ( e Φ ) for DPC compound were found to be 0.739 cm 2 V −1 s −1 and 0.319 cm 2 V −1 s −1 , respectively, at Φ = 0 • . On the other hand, in the case of BPSC crystal, comparatively larger anisotropic electron mobility (0.709 cm 2 V −1 s −1 at Φ = 0 • and Φ = 179.90 • ) than the hole mobility (0.208 cm 2 V −1 s −1 at Φ = 127.19 • and Φ = 307.10 • ) was noted. Similarly, in ETCC, the parallel dimers were found to contribute maximum h Φ and e Φ of 0.052 and 0.102 cm 2 V −1 s −1 , respectively, at Φ = 0 • . The substitution of -SPh in BPSC and -OCH 3 and -CO 2 CH 2 CH 3 in ETCC have relatively more impact on band reduction than -OPh in DPC, thus facilitating electron transport in BPSC and ETCC.

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“…For example, the single crystal of pentacene, which is a linearly fused acenes shows field effect mobility of 2.3 cm 2 V −1 s −1 at room temperature on Si/SiO 2 substrate. Similarly, single crystals of tetrabenzotetracene possess highest measured mobility up to 0.81 cm 2 V −1 s −1 . Rubrene, which is an extended tetracene shows ambipolar behavior with single‐crystal hole (electron) mobility of the order of 1.54 (0.28) cm 2 V −1 s −1 .…”

Section: Introductionmentioning

confidence: 98%

Indolocarbazole (IC) Derivatives as Promising p‐type Organic Semiconductors: A First‐Principle Study of Their Anisotropic Charge Mobilities

2018

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We present a detailed theoretical study of the structural, charge transport, and optical properties of three indolocarbazole derivatives, viz., 11, 12‐Dihydroindolo[2, 3‐a]carbazole (DIC), 5, 10‐dimethyl‐5,10‐dihydrobenzo[a]indolo[2, 3‐c]carbazole (DMDBIC), and 2,11‐dimethoxydibenzo[2, 3:5,6]pyrrolizino[1, 7‐bc]indolo[1, 2,3‐lm]carbazole (DMDPIC). DFT calculations along with previously reported x‐ray crystal structures reveal that the studied compounds are planar and do not undergo significant changes in structure upon oxidation or reduction. The maximum hole anisotropic charge mobilities for DIC was found to be 0.338 cm2 V−1 s−1 at Φ=175.89° and 355.81° and the maximum electron mobility was 0.181 cm2 V−1 s−1 at Φ=85.94° and 265.85°. For DMDBIC, the predicted maximum anisotropic hole, and electron mobility was 0.501 cm2 V−1 s−1 and 0.775 cm2 V−1 s−1, respectively at Φ=56.72° and 236.63°, while for DMDPIC the predicted maximum anisotropic hole and electron mobility as 1.586 cm2 V−1 s−1 and 0.594 cm2 V−1 s−1, respectively at Φ=0° and 180.0°. The calculated mobilities show that these compounds may be suitable candidates as a p‐type organic semiconductor with better stability than acene compounds.

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Contorted tetrabenzoacenes of varied conjugation: charge transport study with single-crystal field-effect transistors

Abstract: A series of nonplanar tetrabenzo-fused acenes exhibited a hole mobility from 0.044 cm2 V−1 s−1 up to 0.81 cm2 V−1 s−1 in their single crystal field-effect transistors.

Cited by 21 publications

References 61 publications

Polysubstituted Hexa-cata-hexabenzocoronenes: Syntheses, Characterization, and Their Potential as Semiconducting Materials in Transistor Applications

Polysubstituted Hexa-cata-hexabenzocoronenes: Syntheses, Characterization, and Their Potential as Semiconducting Materials in Transistor Applications

Anisotropic charge transport properties of chrysene derivatives as organic semiconductor: A computational study

Indolocarbazole (IC) Derivatives as Promising p‐type Organic Semiconductors: A First‐Principle Study of Their Anisotropic Charge Mobilities

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