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Dual-State Ambipolar Charge Transport in Antiaromatic [4]cyclodibenzopentalene Single-Molecule Nanohoops

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Dual-State Ambipolar Charge Transport in Antiaromatic [4]cyclodibenzopentalene Single-Molecule Nanohoops. / Feng, Sai; Almughathawi, Renad; Weber, Andrej et al.
In: Journal of the American Chemical Society, Vol. 147, No. 22, 04.06.2025, p. 18475-18483.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Feng, S, Almughathawi, R, Weber, A, Hou, S, Zhang, C, Wössner, JS, Esser, B, Lambert, C, Wu, Q, Li, Y & Li, J 2025, 'Dual-State Ambipolar Charge Transport in Antiaromatic [4]cyclodibenzopentalene Single-Molecule Nanohoops', Journal of the American Chemical Society, vol. 147, no. 22, pp. 18475-18483. https://doi.org/10.1021/jacs.4c17115

APA

Feng, S., Almughathawi, R., Weber, A., Hou, S., Zhang, C., Wössner, J. S., Esser, B., Lambert, C., Wu, Q., Li, Y., & Li, J. (2025). Dual-State Ambipolar Charge Transport in Antiaromatic [4]cyclodibenzopentalene Single-Molecule Nanohoops. Journal of the American Chemical Society, 147(22), 18475-18483. https://doi.org/10.1021/jacs.4c17115

Vancouver

Feng S, Almughathawi R, Weber A, Hou S, Zhang C, Wössner JS et al. Dual-State Ambipolar Charge Transport in Antiaromatic [4]cyclodibenzopentalene Single-Molecule Nanohoops. Journal of the American Chemical Society. 2025 Jun 4;147(22):18475-18483. Epub 2025 May 19. doi: 10.1021/jacs.4c17115

Author

Feng, Sai ; Almughathawi, Renad ; Weber, Andrej et al. / Dual-State Ambipolar Charge Transport in Antiaromatic [4]cyclodibenzopentalene Single-Molecule Nanohoops. In: Journal of the American Chemical Society. 2025 ; Vol. 147, No. 22. pp. 18475-18483.

Bibtex

@article{9f0d5e2ae97c4e349728df7c47bb23a1,
title = "Dual-State Ambipolar Charge Transport in Antiaromatic [4]cyclodibenzopentalene Single-Molecule Nanohoops",
abstract = "Antiaromatic compounds are of great interest due to their narrow highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) gaps, high reactivity, and enhanced charge mobility, yet their role in single-molecule electronics is still not well understood. Using electrochemically controlled scanning tunneling microscopy break junction (ECSTM-BJ) measurements, we compared the energy-alignment-dependent conductance of the aromatic [10]cycloparaphenylene ([10]CPP) and the antiaromatic [4]cyclodibenzopentalene ([4]CDBP). While [10]CPP showed a single conductance state via the HOMO, [4]CDBP exhibited two distinct states involving both the HOMO and LUMO. Our analysis and DFT calculations attribute this dual-state behavior to unique anchoring mode and energy-level realignment within a narrow HOMO-LUMO gap. This property enables electron- and hole-dominated pathways that depend on the anchoring configuration and coexist at a fixed gate potential. This phenomenon, also observed in the [4]CDBP⊃C60 structure, highlights the potential of antiaromatic molecules for advanced molecular electronics.",
author = "Sai Feng and Renad Almughathawi and Andrej Weber and Songjun Hou and Chengyang Zhang and W{\"o}ssner, {Jan S.} and Birgit Esser and Colin Lambert and Qingqing Wu and Yueqi Li and Jinghong Li",
year = "2025",
month = jun,
day = "4",
doi = "10.1021/jacs.4c17115",
language = "English",
volume = "147",
pages = "18475--18483",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "AMER CHEMICAL SOC",
number = "22",

}

RIS

TY - JOUR

T1 - Dual-State Ambipolar Charge Transport in Antiaromatic [4]cyclodibenzopentalene Single-Molecule Nanohoops

AU - Feng, Sai

AU - Almughathawi, Renad

AU - Weber, Andrej

AU - Hou, Songjun

AU - Zhang, Chengyang

AU - Wössner, Jan S.

AU - Esser, Birgit

AU - Lambert, Colin

AU - Wu, Qingqing

AU - Li, Yueqi

AU - Li, Jinghong

PY - 2025/6/4

Y1 - 2025/6/4

N2 - Antiaromatic compounds are of great interest due to their narrow highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) gaps, high reactivity, and enhanced charge mobility, yet their role in single-molecule electronics is still not well understood. Using electrochemically controlled scanning tunneling microscopy break junction (ECSTM-BJ) measurements, we compared the energy-alignment-dependent conductance of the aromatic [10]cycloparaphenylene ([10]CPP) and the antiaromatic [4]cyclodibenzopentalene ([4]CDBP). While [10]CPP showed a single conductance state via the HOMO, [4]CDBP exhibited two distinct states involving both the HOMO and LUMO. Our analysis and DFT calculations attribute this dual-state behavior to unique anchoring mode and energy-level realignment within a narrow HOMO-LUMO gap. This property enables electron- and hole-dominated pathways that depend on the anchoring configuration and coexist at a fixed gate potential. This phenomenon, also observed in the [4]CDBP⊃C60 structure, highlights the potential of antiaromatic molecules for advanced molecular electronics.

AB - Antiaromatic compounds are of great interest due to their narrow highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) gaps, high reactivity, and enhanced charge mobility, yet their role in single-molecule electronics is still not well understood. Using electrochemically controlled scanning tunneling microscopy break junction (ECSTM-BJ) measurements, we compared the energy-alignment-dependent conductance of the aromatic [10]cycloparaphenylene ([10]CPP) and the antiaromatic [4]cyclodibenzopentalene ([4]CDBP). While [10]CPP showed a single conductance state via the HOMO, [4]CDBP exhibited two distinct states involving both the HOMO and LUMO. Our analysis and DFT calculations attribute this dual-state behavior to unique anchoring mode and energy-level realignment within a narrow HOMO-LUMO gap. This property enables electron- and hole-dominated pathways that depend on the anchoring configuration and coexist at a fixed gate potential. This phenomenon, also observed in the [4]CDBP⊃C60 structure, highlights the potential of antiaromatic molecules for advanced molecular electronics.

U2 - 10.1021/jacs.4c17115

DO - 10.1021/jacs.4c17115

M3 - Journal article

VL - 147

SP - 18475

EP - 18483

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 22

ER -