Cumulene Wires Display Increasing Conductance with Increasing LengthClick to copy article linkArticle link copied!
- Yaping ZangYaping ZangDepartment of Applied Physics and Applied Mathematics, Columbia University, New York, New York 10027, United StatesMore by Yaping Zang
- Tianren FuTianren FuDepartment of Chemistry, Columbia University, New York, New York 10027, United StatesMore by Tianren Fu
- Qi Zou*Qi Zou*E-mail: (Q.Z.) [email protected]Department of Chemistry, Columbia University, New York, New York 10027, United StatesShanghai Key Laboratory of Materials Protection and Advanced Materials in Electric Power, Shanghai University of Electric Power, Shanghai 200090, ChinaMore by Qi Zou
- Fay NgFay NgDepartment of Chemistry, Columbia University, New York, New York 10027, United StatesMore by Fay Ng
- Hexing LiHexing LiShanghai Key Laboratory of Materials Protection and Advanced Materials in Electric Power, Shanghai University of Electric Power, Shanghai 200090, ChinaMore by Hexing Li
- Michael L. SteigerwaldMichael L. SteigerwaldDepartment of Chemistry, Columbia University, New York, New York 10027, United StatesMore by Michael L. Steigerwald
- Colin Nuckolls*Colin Nuckolls*Email: (C.N.) [email protected]Department of Chemistry, Columbia University, New York, New York 10027, United StatesMore by Colin Nuckolls
- Latha Venkataraman*Latha Venkataraman*Email: (L.V.) [email protected]Department of Applied Physics and Applied Mathematics, Columbia University, New York, New York 10027, United StatesDepartment of Chemistry, Columbia University, New York, New York 10027, United StatesMore by Latha Venkataraman
Abstract

One-dimensional sp-hybridized carbon wires, including cumulenes and polyynes, can be regarded as finite versions of carbynes. They are likely to be good candidates for molecular-scale conducting wires as they are predicted to have a high-conductance. In this study, we first characterize the single-molecule conductance of a series of cumulenes and polyynes with a backbone ranging in length from 4 to 8 carbon atoms, including [7]cumulene, the longest cumulenic carbon wire studied to date for molecular electronics. We observe different length dependence of conductance when comparing these two forms of carbon wires. Polyynes exhibit conductance decays with increasing molecular length, while cumulenes show a conductance increase with increasing molecular length. Their distinct conducting behaviors are attributed to their different bond length alternation, which is supported by theoretical calculations. This study confirms the long-standing theoretical predictions on sp-hybridized carbon wires and demonstrates that cumulenes can form highly conducting molecular wires.
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- Yueze Gao, Edmund Leary, Lucía Palomino-Ruiz, José M. Malagón, M. Teresa González, Maximilian Krempe, Matthew Johnson, Rik R. Tykwinski. Length-Dependent Conduction of Polyynes: Searching for the Limit of the Tunneling Regime. Journal of the American Chemical Society 2025, 147
(5)
, 4052-4059. https://doi.org/10.1021/jacs.4c12895
- Mehrdad Shiri, Haixin Zhang, Kun Wang. No More Conductance Decay: Toward Efficient Long-Range Transport in Molecular Wires. ACS Applied Electronic Materials 2024, 6
(12)
, 8626-8639. https://doi.org/10.1021/acsaelm.4c00415
- Jiung Jang, Hyo Jae Yoon. Long-Range Charge Transport in Molecular Wires. Journal of the American Chemical Society 2024, 146
(47)
, 32206-32221. https://doi.org/10.1021/jacs.4c11431
- Jianqin Tang, Chenyang Hu, Agamemnon E. Crumpton, Maximilian Dietz, Debotra Sarkar, Liam P. Griffin, Jose M. Goicoechea, Simon Aldridge. Syntheses, Geometric and Electronic Structures of Inorganic Cumulenes. Journal of the American Chemical Society 2024, 146
(45)
, 30778-30783. https://doi.org/10.1021/jacs.4c13231
- Brent Lawson, Efrain Vidal, Jr., Sigifredo Luna, Michael M. Haley, Maria Kamenetska. Extreme Anomalous Conductance Enhancement in Neutral Diradical Acene-like Molecular Junctions. ACS Nano 2024, 18
(42)
, 29059-29066. https://doi.org/10.1021/acsnano.4c10183
- Liang Li, Shayan Louie, Nicholas M. Orchanian, Colin Nuckolls, Latha Venkataraman. Long-Range Gating in Single-Molecule One-Dimensional Topological Insulators. Journal of the American Chemical Society 2024, 146
(24)
, 16920-16925. https://doi.org/10.1021/jacs.4c05699
- Meng-Meng Guo, Yuxuan Jiang, Jin-Yun Wang, Zhong-Ning Chen, Shimin Hou, Qian-Chong Zhang. Effectively Enhancing the Conductance of Asymmetric Molecular Wires by Aligning the Energy Level and Symmetrizing the Coupling. Langmuir 2024, 40
(7)
, 3759-3765. https://doi.org/10.1021/acs.langmuir.3c03530
- Jie-Ren Deng, M. Teresa González, He Zhu, Harry L. Anderson, Edmund Leary. Ballistic Conductance through Porphyrin Nanoribbons. Journal of the American Chemical Society 2024, 146
(6)
, 3651-3659. https://doi.org/10.1021/jacs.3c07734
- Mauro Marongiu, Tracy Ha, Sara Gil-Guerrero, Kavita Garg, Marcos Mandado, Manuel Melle-Franco, Ismael Diez-Perez, Aurelio Mateo-Alonso. Molecular Graphene Nanoribbon Junctions. Journal of the American Chemical Society 2024, 146
(6)
, 3963-3973. https://doi.org/10.1021/jacs.3c11340
- Liang Li, Claudia R. Prindle, Wanzhuo Shi, Colin Nuckolls, Latha Venkataraman. Radical Single-Molecule Junctions. Journal of the American Chemical Society 2023, 145
(33)
, 18182-18204. https://doi.org/10.1021/jacs.3c04487
- Liang Li, Colin Nuckolls, Latha Venkataraman. Designing Long and Highly Conducting Molecular Wires with Multiple Nontrivial Topological States. The Journal of Physical Chemistry Letters 2023, 14
(22)
, 5141-5147. https://doi.org/10.1021/acs.jpclett.3c01081
- Kai Song, Junfeng Lin, Xuwei Song, Mingliang Zhang, Qianfeng Gu, Yaping Zang, Daoben Zhu. In Situ Creation of Organometallic Molecular Junctions via Terminal Alkynes. The Journal of Physical Chemistry C 2023, 127
(18)
, 8850-8855. https://doi.org/10.1021/acs.jpcc.3c01337
- Liang Li, Shayan Louie, Austin M. Evans, Elena Meirzadeh, Colin Nuckolls, Latha Venkataraman. Topological Radical Pairs Produce Ultrahigh Conductance in Long Molecular Wires. Journal of the American Chemical Society 2023, 145
(4)
, 2492-2498. https://doi.org/10.1021/jacs.2c12059
- Liang Li, Suman Gunasekaran, Yujing Wei, Colin Nuckolls, Latha Venkataraman. Reversed Conductance Decay of 1D Topological Insulators by Tight-Binding Analysis. The Journal of Physical Chemistry Letters 2022, 13
(41)
, 9703-9710. https://doi.org/10.1021/acs.jpclett.2c02812
- Anni Feng, Songjun Hou, Juanzhu Yan, Qingqing Wu, Yongxiang Tang, Yang Yang, Jia Shi, Zong-Yuan Xiao, Colin J. Lambert, Nanfeng Zheng, Wenjing Hong. Conductance Growth of Single-Cluster Junctions with Increasing Sizes. Journal of the American Chemical Society 2022, 144
(34)
, 15680-15688. https://doi.org/10.1021/jacs.2c05856
- Qi Zou, Xuanying Chen, Yu Zhou, Xin Jin, Zhiyun Zhang, Jin Qiu, Rui Wang, Wenjing Hong, Jianhua Su, Da-Hui Qu, He Tian. Photoconductance from the Bent-to-Planar Photocycle between Ground and Excited States in Single-Molecule Junctions. Journal of the American Chemical Society 2022, 144
(22)
, 10042-10052. https://doi.org/10.1021/jacs.2c03671
- Wenjun Xu, Edmund Leary, Sara Sangtarash, Michael Jirasek, M. Teresa González, Kirsten E. Christensen, Lydia Abellán Vicente, Nicolás Agraït, Simon J. Higgins, Richard J. Nichols, Colin J. Lambert, Harry L. Anderson. A Peierls Transition in Long Polymethine Molecular Wires: Evolution of Molecular Geometry and Single-Molecule Conductance. Journal of the American Chemical Society 2021, 143
(48)
, 20472-20481. https://doi.org/10.1021/jacs.1c10747
- Alexandra Siklitskaya, Tomasz Bednarek, James Pogrebetsky, Adam Kubas. An overview of physical and chemical long-range phenomena governed by Friedel oscillations: a bridge between physics and chemistry. Materials Chemistry Frontiers 2025, 9
(4)
, 541-579. https://doi.org/10.1039/D4QM00766B
- Jinlong Ren, Tianchen Li, Zhuang Li, Decheng Kong, Guangcun Shan, KunPeng Dou. Collection of unconventional transport phenomena: natural obstacle or vibrant guiding principle for the design of molecular junctions?. AAPPS Bulletin 2024, 34
(1)
https://doi.org/10.1007/s43673-023-00110-6
- Lorentz Jäntschi. Triple crossed 3 C
26
cyclic cumulene catenane. Fullerenes, Nanotubes and Carbon Nanostructures 2024, 32
(10)
, 962-976. https://doi.org/10.1080/1536383X.2024.2354721
- Tsumugi Miyashita, Sheng He, Paulina Jaimes, Alexey L. Kaledin, Maria Fumanal, Tianquan Lian, Ming Lee Tang. Oligoyne bridges enable strong through-bond coupling and efficient triplet transfer from CdSe QD trap excitons for photon upconversion. The Journal of Chemical Physics 2024, 161
(9)
https://doi.org/10.1063/5.0223478
- Zhong-Yang Chen, Yu-Han Dai, Shi-Nuo Xu, Jian-Feng Yan, Yan-Hou Geng, Yao-Feng Yuan. Synthesis, characterization, and electronic transport properties of o-carborane-bridged thiophene derivatives. Journal of Organometallic Chemistry 2024, 1016 , 123234. https://doi.org/10.1016/j.jorganchem.2024.123234
- Afton Gustafson, Sophia Sburlati, Bart Kahr. Computed Gyration Tensors of Knotted Chiral and Achiral Topological Stereoisomers of C
60
Cyclocarbons. ChemPhysChem 2024, 25
(14)
https://doi.org/10.1002/cphc.202400277
- Elda Sala, Valerio F. Annese, Bozheng Sun, Rik R. Tykwinski, Carlo S. Casari, Mario Caironi. Enhancement of Stability to Light in Field-Effect Transistors Based on Cumulenic sp-carbon Wires by Opaque Gating Electrodes. 2024, 1-4. https://doi.org/10.1109/FLEPS61194.2024.10604255
- Zheng Zhou, Matthew A. Johnson, Zheng Wei, Martina U. Bühringer, Marc H. Garner, Rik Tykwinski, Marina A. Petrukhina. Bending a Cumulene with Electrons: Stepwise Chemical Reduction and Structural Study of a Tetraaryl[4]Cumulene. Chemistry – A European Journal 2024, 30
(26)
https://doi.org/10.1002/chem.202304145
- David Bain, Julia Chang, Yihuan Lai, Thomas Khazanov, Phillip J. Milner, Andrew J. Musser. Torsional Disorder in Tetraphenyl [3]-Cumulenes: Insight into Excited State Quenching. Photochem 2024, 4
(1)
, 138-150. https://doi.org/10.3390/photochem4010008
- Cheng Liu, Cheng Fu, Lingyu Tang, Jianghua Wu, Zhangyan Mu, Yamei Sun, Yanghang Pan, Bailin Tian, Kai Bao, Jing Ma, Qiyuan He, Mengning Ding. Molecule-based vertical transistor via intermolecular charge transport through π-π stacking. Nano Research 2023, 1 https://doi.org/10.1007/s12274-023-6252-3
- Fei Chen, Qing-Man Liang, Long-Xing Lin, Qian-Chong Zhang, Yang Yang. Recent progress in tuning charge transport in single-molecule junctions by substituents. Journal of Materials Chemistry C 2023, 11
(42)
, 14515-14526. https://doi.org/10.1039/D3TC02035E
- Pilarisetty Tarakeshwar, Moreno Meneghetti, Jun Wu, Robert Lloyd Whetten, Miguel José Yacaman, Peter R. Buseck. Stabilization of reactive sp carbon chains. Carbon 2023, 215 , 118493. https://doi.org/10.1016/j.carbon.2023.118493
- Akihito Konishi, Shizuka Imai, Shoya Satake, Kouji Chiba, Makoto Yasuda. Synthesis and Characterization of Hexafluorocyclopentane‐Bridged Bisbutatrienes as Models for Longer Cumulenes: Various Transformations for the Construction of π‐Conjugated Frameworks. Chemistry – A European Journal 2023, 29
(40)
https://doi.org/10.1002/chem.202301255
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(26)
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(25)
, 10573-10583. https://doi.org/10.1039/D3NR01034A
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(3)
, 100115. https://doi.org/10.1016/j.esci.2023.100115
- Yi Mu, Jie Yu, Rui Hu, Cui-Hong Wang, Cai Cheng, Bang-Pin Hou. Ab initio
study revealing remarkable oscillatory effects and negative differential resistance in the molecular device of silicon carbide chains. Physical Chemistry Chemical Physics 2023, 25
(19)
, 13265-13274. https://doi.org/10.1039/D2CP05677A
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(19)
, 13673-13682. https://doi.org/10.1039/D2CP06030B
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(13)
, 9607-9616. https://doi.org/10.1039/D3CP00366C
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(11)
, 5305-5316. https://doi.org/10.1039/D2NR05670D
- Matthew A. Johnson, Jakob A. Meckes, Martina U. Bühringer, Zheng Zhou, Yoshiyuki Kuwatani, Michael J. Ferguson, Zheng Wei, Masahiko Iyoda, Marina A. Petrukhina, Rik R. Tykwinski. On the road to stable, isolable [4]cumulenes: Reactivity and cyclization reactions. Journal of Physical Organic Chemistry 2023, 36
(2)
https://doi.org/10.1002/poc.4454
- Ajun Tang, Yunpeng Li, Rui Wang, Jiawei Yang, Chaoqi Ma, Zhi Li, Qi Zou, Hongxiang Li. Charge transport of F4TCNQ with different electronic states in single-molecule junctions. Chemical Communications 2023, 59
(10)
, 1305-1308. https://doi.org/10.1039/D2CC06341G
- Guowei Yang. Synthesis, properties, and applications of carbyne nanocrystals. Materials Science and Engineering: R: Reports 2022, 151 , 100692. https://doi.org/10.1016/j.mser.2022.100692
- Zixiao Wang, Julio L. Palma, Hui Wang, Junzhi Liu, Gang Zhou, M. R. Ajayakumar, Xinliang Feng, Wei Wang, Jens Ulstrup, Alexei A. Kornyshev, Yueqi Li, Nongjian Tao. Electrochemically controlled rectification in symmetric single-molecule junctions. Proceedings of the National Academy of Sciences 2022, 119
(39)
https://doi.org/10.1073/pnas.2122183119
- Jasveer S. Dhindsa, Erin L. Cotterill, Francis L. Buguis, Michael Anghel, Paul D. Boyle, Joe B. Gilroy. Blending the Optical and Redox Properties of Oligoynes and Boron Difluoride Formazanates. Angewandte Chemie 2022, 134
(39)
https://doi.org/10.1002/ange.202208502
- Jasveer S. Dhindsa, Erin L. Cotterill, Francis L. Buguis, Michael Anghel, Paul D. Boyle, Joe B. Gilroy. Blending the Optical and Redox Properties of Oligoynes and Boron Difluoride Formazanates. Angewandte Chemie International Edition 2022, 61
(39)
https://doi.org/10.1002/anie.202208502
- Liang Li, Jonathan Z. Low, Jan Wilhelm, Guanming Liao, Suman Gunasekaran, Claudia R. Prindle, Rachel L. Starr, Dorothea Golze, Colin Nuckolls, Michael L. Steigerwald, Ferdinand Evers, Luis M. Campos, Xiaodong Yin, Latha Venkataraman. Highly conducting single-molecule topological insulators based on mono- and di-radical cations. Nature Chemistry 2022, 14
(9)
, 1061-1067. https://doi.org/10.1038/s41557-022-00978-1
- Marcin Gronowski, Robert Kołos. A DFT Study on the Excited Electronic States of Cyanopolyynes: Benchmarks and Applications. Molecules 2022, 27
(18)
, 5829. https://doi.org/10.3390/molecules27185829
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(7)
, 077303. https://doi.org/10.1088/1674-1056/ac4cbf
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(21)
, 13094-13101. https://doi.org/10.1039/D1CP02044G
- Matthew A. Johnson, Max M. Martin, Kévin Cocq, Norbert Jux, Michael J. Ferguson, Rik R. Tykwinski. Acylation of Hexaphenylbenzene for the Synthesis of [5]Cumulenes. European Journal of Organic Chemistry 2022, 2022
(17)
https://doi.org/10.1002/ejoc.202101467
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(15)
https://doi.org/10.1002/adma.202110468
- Nina Sadlej-Sosnowska, Agnieszka Ocios-Bębenek, Jan Cz. Dobrowolski, Dariusz Boczar. Geometrical, electrical, and energetic parameters of hetero-disubstituted cumulenes and polyynes in the presence and absence of the external electric field. Structural Chemistry 2022, 33
(2)
, 479-490. https://doi.org/10.1007/s11224-021-01858-z
- AbhayRam Balakrishnan, S. Vijayakumar. Highly delocalised molecular orbitals in boron-, carbon- and nitrogen-based linear chains: a DFT study. Molecular Physics 2022, 120
(6)
https://doi.org/10.1080/00268976.2021.2020923
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(24)
, 2573-2578. https://doi.org/10.1002/cphc.202100634
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(45)
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(21)
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(20)
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(35)
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(33)
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(24)
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(8)
, 4777-4783. https://doi.org/10.1039/D0CP06321E
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