Preparation and use of organic molecules based on monolateral methylthio-anchored 5,9-dioxy-13B-borannulene[3,2,1-de]anthracene

Abstract

This invention discloses the preparation and application of an organic molecule based on a unilateral methylthio group anchoring 5,9-dioxo-13B-boronanaphthalo[3,2,1-DE]anthracene. The organic molecule based on this invention, with the unilateral methylthio group anchoring 5,9-dioxo-13B-boronanaphthalo[3,2,1-DE]anthracene, has the structure shown below. The boron in this type of molecule can be anchored to gold atoms. During the construction of molecular wires, the presence of two anchoring groups and the strong intermolecular π-π interactions result in three junctional forms, achieving multiple conductivity states within a single molecular framework, demonstrating promising applications in the field of molecular wires.

Description

Technical Field

[0001] This invention belongs to the field of organic electronics technology, and specifically relates to the preparation of an organic molecule based on a single-sided methylthioyl anchoring of 5,9-dioxo-13B-boronnaphthalene[3,2,1-DE]anthracene and its application in single-molecule wires. Background Technology

[0002] Since the rapid development of silicon-based semiconductors, integrated circuits have been evolving towards faster computing speeds, more complex functions, smaller device sizes, and higher integration density. As device feature sizes continue to approach the nanoscale, traditional scaling paths are encountering multiple bottlenecks. On the one hand, further shrinking the size leads to more significant short-channel and quantum tunneling effects, resulting in increased leakage current and static power consumption. On the other hand, engineering limitations such as interconnect delay, thermal management, and manufacturing costs are causing the marginal benefits of continuous scaling to decline. More importantly, silicon-based integrated circuits primarily rely on a top-down fabrication approach to construct devices and interconnects, and their achievable minimum structural size is largely constrained by the intrinsic properties of materials and micro / nano fabrication capabilities. When device sizes approach physical and technological limits, simply relying on traditional scaling strategies is no longer sufficient to continuously meet the dual demands of information technology for high performance and low power consumption.

[0003] Against this backdrop, molecular electronics, as a representative "bottom-up" approach, has attracted widespread attention. Its core idea is to utilize individual molecules as basic circuit elements, achieving specific functions through the designability of molecular structures and quantum effects at the molecular scale, thus providing a potential pathway to overcome the physical limits of silicon-based integrated circuits. Unlike traditional devices that rely on geometric scaling, molecular electronics emphasizes functional integration through the manipulation of chemical structures. Molecules themselves can be designed as wires, rectifiers, switches, or device units with multistable behavior, establishing a correspondence between structure and function at the molecular scale.

[0004] A primary challenge in single-molecule electronics is constructing molecular circuits to characterize the electrical transport properties of organic molecules. Currently, molecular circuits are mainly constructed using scanning tunneling junction (STM-BJ) technology, which provides analytical insights into the electrical transport properties of organic molecules at the single-molecule level. Achieving multiple conductance states based on a single framework is beneficial for improving the integration density of integrated circuits, and the switching between different conductance states can further expand applications in molecular switches and molecular transistors. To achieve multiple conductance states, organic molecules with different types of anchoring groups can be constructed, different stacking configurations can be achieved based on different non-covalent interactions, and different conductance states can be achieved through in-situ electric fields and chemical modulation.

[0005] Therefore, developing an organic molecular framework capable of achieving multiple conductivity states is beneficial for further promoting the development and application of single-molecule electronics. Summary of the Invention

[0006] The primary objective of this invention is to provide an organic molecule based on a unilateral methylthio group anchored to 5,9-dioxo-13B-boronazonaphtho[3,2,1-DE]anthracene.

[0007] Another object of the present invention is to provide a method for preparing the above-mentioned organic molecule based on a unilateral methylthio group anchored to 5,9-dioxo-13B-boronanaphen[3,2,1-DE]anthracene. The present invention yields an organic molecule based on a unilateral methylthio group anchored to 5,9-dioxo-13B-boronanaphen[3,2,1-DE]anthracene, in which boron and methylthio groups can act as anchoring groups to a gold electrode, constructing a molecular wire.

[0008] Another object of the present invention is to provide the application of organic molecules based on unilateral methylthio-anchored 5,9-dioxo-13B-boronazonaphtho[3,2,1-DE]anthracene in the field of molecular wires.

[0009] To achieve the above-mentioned objectives, the present invention provides the following technical solution:

[0010] An organic molecule based on a unilateral methylthio group anchored to 5,9-dioxo-13B-boronazonaphtho[3,2,1-DE]anthracene, the structural formula of which is shown in formula (1) or (2):

[0011]

[0012] Ring A can be an unsubstituted benzene ring, a six-membered heteroaromatic ring containing 1-4 nitrogen atoms, a furan ring, or a thiophene ring.

[0013] Preferably, the ring A is selected from the following structures:

[0014] .

[0015] The present invention also provides a method for preparing an organic molecule based on a unilateral methylthio group anchored to 5,9-dioxo-13B-boronana[3,2,1-DE]anthracene, comprising the following steps: using 5,9-dioxo-13B-boronana[3,2,1-DE]anthracene compounds and 4-methylthiophenylboronic acid pinacol ester or a monobrominated derivative of a monomethylthio-substituted heterocycle as raw materials, and heating the reaction under the conditions of solvent, alkaline substance and tetrakis(triphenylphosphine)palladium as catalyst, an organic molecule with a unilateral methylthio group anchored to 5,9-dioxo-13B-boronana[3,2,1-DE]anthracene can be obtained.

[0016] Preferably, the 5,9-dioxa-13B-borane[3,2,1-DE]anthracene compounds include 7-bromo-5,9-dioxa-13B-borane[3,2,1-DE]anthracene, 7-bromo-2,12-di-tert-butyl-5,9-dioxa-13B-borane[3,2,1-DE]anthracene, 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)-5,9-dioxa-13B-borane[3,2,1-DE]anthracene, or 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)-2,12-di-tert-butyl-5,9-dioxa-13B-borane[3,2,1-DE]anthracene.

[0017] Preferably, the alkaline substance is potassium carbonate.

[0018] Preferably, the solvent is a mixture of toluene, ethanol and water.

[0019] More preferably, the volume ratio of toluene:ethanol:water is 3:1:1.

[0020] Preferably, the heating reaction is carried out at 100~110℃ for 3~12 hours.

[0021] Preferably, the molar ratio of the 5,9-dioxo-13B-boronaphthalo[3,2,1-DE]anthracene compound to 4-methylthiophenylboronic acid pinacol ester or a monobromosubstituted heterocyclic compound is 1:1.

[0022] Specifically, when the 7-bromo-5,9-dioxa-13B-borane[3,2,1-DE]anthracene or 7-bromo-2,12-di-tert-butyl-5,9-dioxa-13B-borane[3,2,1-DE]anthracene is reacted with 4-methylthiophenylboronic acid pinacol ester as a raw material, the molar ratio of the two is 1:1; the 7-(4,4,5,5-tetramethyl-1,3,2-dioxa-1 ... When borane-2-yl)-5,9-dioxa-13B-borane[3,2,1-DE]anthracene or 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)-2,12-di-tert-butyl-5,9-dioxa-13B-borane[3,2,1-DE]anthracene is reacted with a monobromosubstituted heterocyclic compound of monomethylthioyl substituted form as a starting material, the molar ratio of the two is 1:1.

[0023] This invention provides an organic molecule based on a single-sided methylthio-anchored 5,9-dioxo-13B-boronnaphthalene[3,2,1-DE]anthracene as a functional unit to construct molecular wires.

[0024] Preferably, the application includes: constructing a single-molecule device with valence-bonded conjugated transport channels by coupling a single molecule B-Au and S-Au; constructing a head-to-head π-π stacked supramolecular device with valence-bonded conjugated and spatially conjugated transport channels by coupling two molecules through B-Au and S-Au respectively; or, constructing a head-to-tail π-π stacked supramolecular device with spatially conjugated transport channels by coupling two molecules through S-Au.

[0025] Preferably, the application includes: constructing Au-S-5,9-dioxo-13B-boranenaphtho[3,2,1-DE]anthracene-B-Au single-molecule devices using STM-BJ technology; constructing Au-S-5,9-dioxo-13B-boranenaphtho[3,2,1-DE]anthracene-5,9-dioxo-13B-boranenaphtho[3,2,1-DE]anthracene-B-Au head-to-head π-π dimer supramolecular devices; or, constructing Au-S-5,9-dioxo-13B-boranenaphtho[3,2,1-DE]anthracene-5,9-dioxo-13B-boranenaphtho[3,2,1-DE]anthracene-S-Au head-to-tail π-π dimer supramolecular devices.

[0026] Compared with the prior art, the present invention has the following advantages and benefits:

[0027] (1) In this invention, an organic molecule based on unilateral methylthio group anchoring 5,9-dioxo-13B-boronazonaphtho[3,2,1-DE]anthracene was synthesized. The boron in this type of molecule can act as an anchoring group to anchor gold atoms.

[0028] (2) The organic molecule synthesized in this invention based on unilateral methylthio group anchoring 5,9-dioxo-13B-boronazonaphtho[3,2,1-DE]anthracene has a planar structure. The molecule can construct supramolecular structures through π-π interactions. The presence of the two anchoring groups, boron and methylthio, promotes the formation of two supramolecular devices, realizing multiple conductivity states under a single molecular framework. Attached Figure Description

[0029] To more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the accompanying drawings used in the description of the embodiments or the prior art will be briefly introduced below.

[0030] Figure 1 The diagram shows the one-dimensional conductivity (A) and two-dimensional conductivity-displacement histogram (B) of BO-SMe at 0.1 V.

[0031] Figure 2 The following are the one-dimensional conductance plot (A) and two-dimensional conductance-displacement histogram (B) of tBO-SMe at 0.1 V.

[0032] Figure 3Two-dimensional diagrams of flicker noise for BO-SMe(A) and tBO-SMe(B).

[0033] Figure 4 The molecular crystal structures of BO-SMe(A) and tBO-SMe(B) are shown.

[0034] Figure 5 The single-molecule junction device structures are BO-SMe(A) and tBO-SMe(B).

[0035] Figure 6 Transmission spectra of single-molecule junction devices of BO-SMe and tBO-SMe.

[0036] Figure 7 Frontier molecular orbital analysis for single-molecule junction devices of BO-SMe(A) and tBO-SMe(B).

[0037] Figure 8 The diagram shows the one-dimensional conductivity (A) and two-dimensional conductivity-displacement histogram (B) of BO-SMe at 0.3 V.

[0038] Figure 9 The one-dimensional conductivity plot (A) and two-dimensional conductivity-displacement histogram (B) of tBO-SMe at 0.3 V are shown.

[0039] Figure 10 Two-dimensional images of scintillation noise for BO-SMe head-to-head π-π stacked molecular junctions (A) and head-to-tail π-π stacked molecular junctions (B).

[0040] Figure 11 The device structures are BO-SMe head-to-head π-π stacked molecular junction (A) and head-to-tail π-π stacked molecular junction (B).

[0041] Figure 12 Transmission spectra of BO-SMe head-to-head π-π stacked molecular junction and head-to-tail π-π stacked molecular junction devices.

[0042] Figure 13 Frontier molecular orbital analysis for BO-SMe head-to-head π-π stacked molecular junction devices.

[0043] Figure 14 Frontier molecular orbital analysis for BO-SMe head-to-tail π-π stacked molecular junction devices. Specific implementation methods

[0044] The present invention will now be described in further detail with reference to the embodiments and accompanying drawings. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. Any changes, modifications, substitutions, combinations, or simplifications made without departing from the spirit and principle of the invention should be considered equivalent substitutions and are included within the scope of protection of the present invention. Furthermore, it should be understood that after reading the teachings of this invention, those skilled in the art can make various alterations or modifications to the invention, and these equivalent forms also fall within the scope defined by the appended claims.

[0045] Example 1

[0046] Preparation of organic molecules based on unilateral methylthio-anchored 5,9-dioxo-13b-boronanapheno[3,2,1-de]anthracene (BO-SMe)

[0047]

[0048] The synthesis route is as follows:

[0049]

[0050] 7-Bromo-5,9-dioxa-13B-boronaphthalo[3,2,1-DE]anthracene (1 mmol), 4-methylthiophenylboronic acid pinacol ester (1 mmol), potassium carbonate (1.5 mmol), and tetrakis(triphenylphosphine)palladium (0.1 mmol) were added to a reaction flask, and the mixture was purged three times. Then, 50 mL of a mixed solvent of toluene, water, and ethanol (toluene:ethanol:water volume ratio 3:1:1) was added, and the mixture was heated to 110 °C and reacted for 6 h. After extraction with dichloromethane and water, the product was concentrated and then subjected to column chromatography to obtain the final product BO-SMe in 68% yield. BO-SMe: 1 H NMR (500 MHz, CD2Cl2) δ8.72 (dd, J = 7.7, 1.5 Hz, 2H), 7.75 (dd, J = 13.2,4.9 Hz, 4H), 7.58 (d, J = 8.3 Hz, 2H), 7.49 (s, 2H), 7.42 (dd, J = 16.5, 7.8Hz, 4H), 2.56 (s, 2H). 13C NMR (101 MHz, CD2Cl2) δ160.62, 157.72, 147.19,139.58, 136.55, 134.53, 133.66, 127.78, 126.45, 122.85, 118.32, 106.53,53.98, 53.71, 53.44, 53.17, 52.90, 15.27. HRMS (C 25 H 17 BO2S): m / z 393.1118 [M +H + ,calcd. 393.1076].

[0051] Example 2

[0052] Preparation of organic molecules based on unilateral methylthio-anchored 2,12-di-tert-butyl-5,9-dioxo-13B-"[3,2,1-DE]anthracene

[0053]

[0054] The synthesis route is as follows:

[0055]

[0056] 7-Bromo-2,12-di-tert-butyl-5,9-dioxa-13B-borane[3,2,1-DE]anthracene (1 mmol), 4-methylthiophenylboronic acid pinacol ester (1 mmol), potassium carbonate (1.5 mmol), and tetrakis(triphenylphosphine)palladium (0.1 mmol) were added to a reaction flask, and the mixture was purged three times. Then, 50 mL of a mixed solvent of toluene, water, and ethanol (toluene:ethanol:water volume ratio 3:1:1) was added, and the mixture was heated to 110 °C and reacted for 6 h. After extraction with dichloromethane and water, the product was concentrated and then subjected to column chromatography to obtain the final product tBO-SMe in 70% yield. tBO-SMe: 1 H NMR (500 MHz, CD2Cl2) δ8.78 (d, J = 2.5 Hz, 2H), 7.82 (dd, J= 8.8, 2.5 Hz, 3H), 7.73 (d, J = 8.5 Hz, 2H), 7.52 (d, J = 8.8 Hz, 2H), 7.46(s, 2H), 7.40 (d, J = 8.5 Hz, 2H), 2.56 (s, 3H), 1.50 (s, 18H). 13C NMR (101MHz, CD2Cl2) δ158.78, 157.92, 146.94, 145.20, 139.46, 136.73, 131.59, 130.28,127.79, 126.49, 117.81, 106.42, 53.97, 53.70, 53.43, 53.16, 52.89, 34.46,31.28, 15.30. HRMS (C 33 H 33 BO2S): m / z 505.2371 [M + H + ,calcd. 505.2367].

[0057] Test Example 1: Determination of Molecular Conductivity Based on Scanning Tunneling Bound Junction (STM-BJ) Technology

[0058] Figure 1 In the diagram, A represents the one-dimensional conductivity of the BO-SMe molecule at 0.1 V. From this one-dimensional conductivity diagram, the high-conductivity peak of BO-SMe is located at 10 V. -2.89 G0, Figure 1 B in the diagram represents the two-dimensional conductivity diagram of the BO-SMe molecule. The two-dimensional conductivity diagram shows a clear conductivity density cloud and a stretching distance of 0.5 nm. The molecular junction length is 1.00 nm.

[0059] Figure 2 In the diagram, A represents the one-dimensional conductivity plot of the tBO-SMe molecule at 0.1 V. The high-conductivity peak of tBO-SMe is located at 10 V from the one-dimensional conductivity plot. -3.03 G0, Figure 2 B in the diagram represents the two-dimensional conductivity diagram of the tBO-SMe molecule. The two-dimensional conductivity diagram shows a clear conductivity density cloud and a stretching distance of 0.43 nm, with a molecular junction length of 0.93 nm.

[0060] Test Example 2: Flicker Noise Analysis

[0061] Figure 3 In the diagram, A represents the flicker noise analysis of BO-SMe. Figure 3 B shows the flicker noise analysis of tBO-SMe. According to literature (Nanoscale, 2018, 10, 3362–3368), the closer the n value of flicker noise is to 1, the more dominant the charge transport is by valence bond conjugated pathways; the closer the n value is to 2, the more dominant the charge transport is by spatial conjugated pathways. Both BO-SMe and tBO-SMe have n values ​​close to 1, indicating that valence bond conjugated pathways dominate.

[0062] Test Example 3: Molecular Crystal Structure

[0063] Figure 4 In the BO-SMe and tBO-SMe crystal structures, the distances between boron and sulfur are 1.04 nm and 1.03 nm, respectively, which are consistent with the lengths of the highly conductive molecular junctions.

[0064] Test Example 4: Optimization of Molecular Device Structure and Frontier Molecular Orbital Analysis with Electrode Coupling

[0065] Figure 5 The optimized BO-SMe and tBO-SMe single-molecule junction device models are shown in the figure. The middle part is the molecular structure, which is currently tilted. 1 is a boron atom, 2 is an oxygen atom, and 3 is a sulfur atom. The boron-oxygen ring is on the left and the benzyl thio group is on the right. The left and right gold electrodes are on both sides. The molecule is anchored to the gold electrodes on both sides through boron and sulfur, respectively, forming a closed circuit after anchoring. Figure 6 It is the transmission spectrum of a single-molecule junction device, where charge transport is dominated by LUMO. Figure 7 The results show that the electron clouds on boron and sulfur are more abundant, forming an effective anchor with the electrodes.

[0066] Test Example 5: Determination of Molecular Conductivity at High Voltage Based on Scanning Tunneling Bound Junction (STM-BJ) Technology

[0067] Figure 8 In the diagram, A represents the one-dimensional conductivity plot of the BO-SMe molecule at 0.3 V. From the one-dimensional conductivity plot, the two π-π stacked conductivity peaks of BO-SMe are located at 10 V and 10 V respectively. -4.59 G0 and 10 -5.70 G0, Figure 8 B in the diagram represents the two-dimensional conductivity of the BO-SMe molecule. The two-dimensional conductivity diagram shows a distinct conductivity density cloud. The molecular junction lengths of the π-π stacked conductivity peaks are 1.05 nm and 1.39 nm, respectively, corresponding to head-to-head π-π stacked and head-to-tail π-π stacked molecular configurations. Figure 9 A represents the one-dimensional conductivity diagram of the tBO-SMe molecule at 0.3 V. The one-dimensional conductivity diagram shows that tBO-SMe exhibits only a high-conductivity state. Figure 9 B is a two-dimensional conductivity diagram of the tBO-SMe molecule, which only shows the high conductivity density cloud.

[0068] Test Example 6: Flicker Noise Analysis

[0069] Figure 10 In the figure, A represents the scintillation noise of the head-to-head π-π stacked conductance peaks, and n has a value of 1.64, which is between 1 and 2. Charge transport is dominated by both valence bond conjugation and spatial conjugation. Figure 10 In the figure, B is the head-to-tail π-π stacked conductivity peak with an n value of 1.98, and charge transport is dominated by spatial conjugation.

[0070] Test Example 7: Optimization of Molecular Device Structure and Frontier Molecular Orbital Analysis with Electrode Coupling

[0071] Figure 11 Device models for optimized BO-SMe head-to-head π-π stacked molecular junctions and head-to-tail π-π stacked molecular junctions. Figure 12 The transmission spectra of the three device configurations of BO-SMe show that, under zero bias voltage, the transmission probability of the single-molecule junction is higher than that of the head-to-head π-π stacked molecular junction and the head-to-tail π-π stacked molecular junction. The contribution of the HOMO orbitals to charge transport in the head-to-head π-π stacked molecular junction and the head-to-tail π-π stacked molecular junction is slightly greater than that of the LUMO orbitals. Figure 13 The distribution of HOMO and LUMO orbitals in head-to-head π-π stacked molecular junction devices is shown. HOMO is mainly distributed on one molecule with a small amount of spatial conjugation, while LUMO is distributed on two molecules through spatial conjugation. This verifies that valence bond conjugation and spatial conjugation jointly dominate charge transport. Figure 14 The distribution of HOMO and LUMO orbitals in a head-to-tail π-π stacked molecular junction device was shown. The electron clouds of both HOMO and LUMO were spatially conjugated and delocalized on the two molecules, verifying that spatial conjugation dominates charge transport.

[0072] The above data indicate that this invention synthesizes organic molecules based on boron and sulfur as anchoring groups, and applies them to organic single-molecule wires. These organic molecules, using boron and sulfur as anchoring groups, form single-molecule devices with effective valence bond conjugation transport. Combined with the characteristics of planar structures, they can form π-π stacked supramolecular devices, obtaining two additional conductivity states through anchoring conditions different from the electrodes, and achieving triple conductivity states based on a single molecular framework.

[0073] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and not to limit them. Although the present invention has been described in detail with reference to preferred embodiments, those skilled in the art should understand that modifications or equivalent substitutions can still be made to the technical solutions of the present invention, and these modifications or equivalent substitutions cannot cause the modified technical solutions to deviate from the spirit and scope of the technical solutions of the present invention.

Claims

1. An organic molecule based on a unilateral methylthio group anchoring 5,9-dioxo-13B-boronazonaphtho[3,2,1-DE]anthracene, characterized in that, Its structure is shown in equation (1) or (2): ， Ring A can be an unsubstituted benzene ring, a six-membered heteroaromatic ring containing 1-4 nitrogen atoms, a furan ring, or a thiophene ring.

2. The organic molecule based on unilateral methylthioyl-anchored 5,9-dioxo-13B-boronazonaphtho[3,2,1-DE]anthracene according to claim 1, characterized in that, The ring A is selected from the following structures: 。 3. The method for preparing the organic molecule based on unilateral methylthio-anchored 5,9-dioxo-13B-boronazonaphtho[3,2,1-DE]anthracene according to claim 1, characterized in that, The process includes the following steps: using 5,9-dioxo-13B-boronana[3,2,1-DE]anthracene compounds and 4-methylthiophenylboronic acid pinacol ester or monobromosubstituted heterocyclic compounds with monomethylthio groups as raw materials, the mixture is heated under conditions of solvent, alkaline substance and tetra(triphenylphosphine)palladium as catalyst to obtain an organic molecule based on 5,9-dioxo-13B-boronana[3,2,1-DE]anthracene anchored by a mono-side methylthio group.

4. The preparation method according to claim 3, characterized in that, The 5,9-dioxa-13B-borane[3,2,1-DE]anthracene compounds include 7-bromo-5,9-dioxa-13B-borane[3,2,1-DE]anthracene, 7-bromo-2,12-di-tert-butyl-5,9-dioxa-13B-borane[3,2,1-DE]anthracene, 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)-5,9-dioxa-13B-borane[3,2,1-DE]anthracene, or 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)-2,12-di-tert-butyl-5,9-dioxa-13B-borane[3,2,1-DE]anthracene.

5. The preparation method according to claim 3, characterized in that, The alkaline substance is potassium carbonate; the solvent is a mixture of toluene, ethanol and water; the volume ratio of toluene:ethanol:water is 3:1:

1.

6. The preparation method according to claim 3, characterized in that, The heating reaction is carried out at 100~110℃ for 3~12 hours.

7. The preparation method according to claim 3, characterized in that, The molar ratio of the 5,9-dioxo-13B-boronaphthalo[3,2,1-DE]anthracene compound to 4-methylthiophenylboronic acid pinacol ester or a monobromosubstituted heterocyclic compound of monomethylthioyl is 1:

1.

8. The use of the organic molecule based on unilateral methylthio-anchored 5,9-dioxo-13B-boronazonaphtho[3,2,1-DE]anthracene as a functional unit in constructing molecular wires, as described in claim 1 or 2.

9. The application according to claim 8, characterized in that, The applications include: constructing single-molecule devices with valence-bonded conjugated transport channels by coupling B-Au and S-Au molecules; constructing head-to-head π-π stacked supramolecular devices with valence-bonded conjugated and spatially conjugated transport channels by coupling two molecules through B-Au and S-Au respectively; or constructing head-to-tail π-π stacked supramolecular devices with spatially conjugated transport channels by coupling two molecules through S-Au.

10. The application according to claim 8, characterized in that, The applications include: constructing Au-S-5,9-dioxo-13B-boranenaphtho[3,2,1-DE]anthracene-B-Au single-molecule devices using STM-BJ technology; constructing Au-S-5,9-dioxo-13B-boranenaphtho[3,2,1-DE]anthracene-5,9-dioxo-13B-boranenaphtho[3,2,1-DE]anthracene-B-Au head-to-head π-π dimer supramolecular devices; or, constructing Au-S-5,9-dioxo-13B-boranenaphtho[3,2,1-DE]anthracene-5,9-dioxo-13B-boranenaphtho[3,2,1-DE]anthracene-S-Au head-to-tail π-π dimer supramolecular devices.

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