Synthesis and Properties of Sulfur-Containing Graphene Nanoribbons

doi:10.6023/cjoc202604043

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (9): 3697-3703.DOI: 10.6023/cjoc202604043 Previous Articles Next Articles

ARTICLE

硫杂石墨烯纳米条带的合成与性质研究

沈义函^a^,^†, 张瑞影^a^,^b^,^†, 高捷龙^a, 李明港^a, 李远明^a^,^b^,^*(), 叶克印^a^,^*()

^a 福州大学化学学院有机合成与功能福建省高校重点实验室福州 350108
^b 福州大学化学学院能源与环境光催化国家重点实验室福州 350116

收稿日期:2026-04-28 修回日期:2026-06-07 发布日期:2026-07-14
通讯作者: 李远明, 叶克印
作者简介:
^† 共同第一作者
基金资助:
福建省本科高校教育教学研究重大项目(FBJY20250332); 福州大学研究生教育教学改革研究重点项目(FYCG2025005); 福州大学研究生教育教学改革研究重点项目(FYAI2025019); 福州大学化学学院化学拔尖人才创新训练计划(HXBJ202402)

Synthesis and Properties of Sulfur-Containing Graphene Nanoribbons

Yihan Shen^a, Ruiying Zhang^a^,^b, Jielong Gao^a, Minggang Li^a, Yuanming Li^a^,^b^,^*(), Keyin Ye^a^,^*()

^a Key Laboratory of Molecule Synthesis and Function Discovery, College of Chemical, Fuzhou University, Fuzhou 350108
^b State Key Laboratory of Chemistry for NBC Hazards Protection, State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou 350116

Received:2026-04-28 Revised:2026-06-07 Published:2026-07-14
Contact: Yuanming Li, Keyin Ye
About author:
Dedicated to the 100th anniversary of the birth of Professor Xikui Jiang.
^† These authors contributed equally to this work
Supported by:
Major Project of Teaching and Education Research for Undergraduate Universities in Fujian Province(FBJY20250332); Key Project of Graduate Education and Teaching Reform Research of Fuzhou University(FYCG2025005); Key Project of Graduate Education and Teaching Reform Research of Fuzhou University(FYAI2025019); Chemistry Top Talent Innovation Training Program of the College of Chemistry, Fuzhou University(HXBJ202402)

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Abstract

A twisted sulfur-doped graphene nanoribbon (GNR) was successfully synthesized via a sequential Suzuki-Miyaura coupling and Scholl reaction. Oxidation of the incorporated thiophene units to sulfone groups was found to be a highly effective molecular engineering strategy, significantly modulating the photophysical and electrochemical properties of the nanoribbon. Density functional theory (DFT) calculations were employed to elucidate the underlying excited-state dynamics and aromatic characteristics. This work establishes a robust and efficient synthetic route for the preparation of sulfur-doped GNRs with precisely tailored electronic properties.

Key words: graphene nanoribbons, sulfur doping, electrochemical synthesis

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Yihan Shen, Ruiying Zhang, Jielong Gao, Minggang Li, Yuanming Li, Keyin Ye. Synthesis and Properties of Sulfur-Containing Graphene Nanoribbons[J]. Chinese Journal of Organic Chemistry, 2026, 46(9): 3697-3703.

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Fig. & Tab. 7

Figure 1. (a) Axial π-extension of the sulfur-doping GNRs (The tert-butyl groups are omitted for clarity); (b) Chemical, electrochemical, and e-flow Scholl reactions

Scheme 1. Preparation of sulfur-containing graphene nanoribbons AR-9 and ARO-9 Reaction conditions: Condition 1: compound 4 (0.06 mmol), DDQ (2.4 equiv.), CF3SO3H, CH2Cl2; Condition 2: in an undivided cell, a carbon felt anode, a Pt cathode, compound 4 (0.01 mmol), nBu4NBF4 (0.067 mol/L), V(DCM)∶V(TFA)=4∶1, DDQ (10 mol%), r.t., Ecell=1.65 V, 40 min; Condition 3: in an e-flow reactor, a carbon anode, a Ni cathode, compound 4 (0.01 mmol), nBu4NBF4 (0.1 mol/L), V(DCM)∶V(TFA)=4∶1, DDQ (10 mol%), r.t., Ecell=1.65 V, v=0.12 mL/min. a Yield was determined by 1H NMR with 1,3,5-trimethoxybenzene as the internal standard. b Isolated yield.

Figure 2. CV (solid lines) and DPV (dashed lines) of AR-5 (black), AR-9 (red) and ARO-9 (blue) in DCM solution containing 0.1 mol/L nBu4NBF4 at room temperature at a scan rate of 0.3 V/s

Figure 3. (a) UV-vis absorption (b) fluorescence for AR-5, AR-9 and ARO-9 were obtained at 10－5 mol/L in CH2Cl2

Compd.	λ_abs^a/nm	λ_em^a/nm	E_HOMO^b/eV	E_LUMO^b/eV	E_g^b/eV
AR-5	288/346/362	386	－5.26	－1.26	4.00
AR-9	318/377/398	419/438	－5.21	－1.58	3.64
ARO-9	298/441	509	－5.51	－2.24	3.27

Table 1. Photophysical properties of AR-9 and ARO-9.

Figure 4. (a) Stereoisomers of AR-9 and their relative Gibbs free energies. (b) Calculated Gibbs free energies of 5 for the conversion from the (P, M, P) to the (M, P, M)

Figure 5. (a) NICS(1)av of AR-9 and ARO-9 calculated at B3LYP/6-31＋G(d) level. (b) ACID of AR-9 and ARO-9 calculated at B3LYP/6-31G(d) level

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硫杂石墨烯纳米条带的合成与性质研究

Synthesis and Properties of Sulfur-Containing Graphene Nanoribbons

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