Photoisomeric compounds and device comprising the same

Patent metadata

Field	Value
Publication number	US-11545640-B2
Application number	US-202117160174-A
Country	US
Kind code	B2
Filing date	Jan 27, 2021
Priority date	May 24, 2016
Publication date	Jan 3, 2023
Grant date	Jan 3, 2023

Abstract

Disclosed are a series of photoisomeric compounds, preparation method therefor and device comprising the compounds, wherein a photoisomeric compound-graphene molecular junction device is formed by linking the photoisomeric compound to a gap of two-dimensional monolayer graphene having a nano-gap array via an amide covalent bond. When a single photoisomeric compound is bridged to the gap of the two-dimensional monolayer graphene having a nano-gap array, the devices have a reversible light-controlled switching function and a reversible electrically-controlled switching function. A molecular switch device prepared by the method can achieve a high reversibility and a good reproducibility. The number of light-controlled switching cycles can exceed 104, and the number of electrically-controlled switching cycles can reach about 105 or greater. Moreover, the above-mentioned reversible molecular switch device remains stable within a period of more than one year. In addition, flexible non-losable organic memory transistor devices and light-responsive organic transistor devices can be constructed using the above-mentioned series of photoisomeric compounds.

First claim

What is claimed is:

1. A diarylethene-graphene molecular junction device, wherein the molecular junction device comprises a diarylethene compound linked to a gap of a two-dimensional monolayer graphene having a nanogap array via an amide covalent bond, wherein the diarylethene compound has any one of the following formulae:

wherein C n represents a linear alkylene group having 3-4 carbon atoms, and H of the alkylene group may be substituted with at least one selected from F, Cl, Br or I.

2. The diarylethene-graphene molecular junction device of claim 1 , wherein the diarylethene compound is any one of the following formulae:

3. A reversible molecular switch device or a transistor device comprising the diarylethene-graphene molecular junction device of claim 1 , wherein:
(1) the reversible molecular switch device is a reversible light-controlled molecular switch device, wherein the reversible light-controlled molecular switch device exhibits a high conductive state under ultraviolet light; and the reversible light-controlled molecular switch device exhibits a low conductive state under visible light;
(2) the reversible molecular switch device is a reversible electrically-controlled molecular switch device comprising a voltage generating means connected to the molecular junction device; wherein the voltage generating means is used to supply:
(a) a voltage of 0.9 V to 1.5 V or a voltage of −0.9 V to −1.5 V; or
(b) a voltage of −0.9 V to 0.9 V, or a voltage of greater than 1.5 V or less than −1.5 V, across the molecular junction device;

provided that the voltage generating means supplies the voltage of 0.9 V to 1.5 V or the voltage of −0.9 V to −1.5 V across the molecular junction device, the reversible electrically-controlled molecular switch device exhibits random switching between a high conductive state and a low conductive state at a temperature of 100 K to 300 K when the electrically-controlled molecular switch device comprises a diarylethene compound of any of Formulae 1-4; and
provided that the voltage generating means supplies a voltage of −0.9 V to 0.9 V, or a voltage greater than 1.5 V or less than −1.5 V across both ends of the molecular junction device, the reversible electrically-controlled molecular switch device exhibits a low conductive state in a voltage range of −0.9 V to 0.9 V and a high conductive state in a voltage of greater than 1.5 V or less than −1.5 V at a temperature of 100 K to 300 K when the reversible electrically-controlled molecular switch device comprises a diarylethene compound of any of Formulae 1-4; or
(3) the reversible molecular switch device is a reversible temperature-controlled molecular switch device; wherein when the reversible temperature-controlled molecular switch device comprises a diarylethene compound of any of Formulae 1-4, the reversible temperature-controlled molecular switch device exhibits a low conductive state at a temperature below 100 K, and a high conductive state at a temperature above 300 K; or
(4) the transistor device comprises the diarylethene-graphene molecular junction device assembled between a dielectric layer and a semiconductor layer of an organic field-effect transistor, or between an electrode and a semiconductor layer of an organic field-effect transistor.

4. The reversible molecular switch device or a transistor device of claim 3 , wherein the reversible light-controlled molecular switch device further includes a visible light generating means and an ultraviolet light generating means, for respectively radiating visible light or ultraviolet light to the reversible light-controlled molecular switch device.

5. The reversible molecular switch device or a transistor device of claim 3 , wherein the diarylethene compound in the reversible electrically-controlled molecular switch device is one of the following formulae:

6. The reversible molecular switch device or a transistor device of claim 3 , wherein the reversible temperature-controlled molecular switch device comprises the diarylethene compound of:

7. The reversible molecular switch device or a transistor device of claim 5 , wherein:
(2) the reversible molecular switch device is the reversible electrically-controlled molecular switch device;
provided that the voltage generating means supplies the voltage of 0.9 V to 1.5 V or the voltage of −0.9 V to −1.5 V across the molecular junction device, the reversible electrically-controlled molecular switch device exhibits random switching between a high conductive state and a low conductive state at a temperature of 160 K to 220 K when the reversible electrically-controlled molecular switch device comprises the diarylethene compound of Formula I-1 or Formula I-2; and
provided that the voltage generating means supplies a voltage of −0.9 V to 0.9 V, or a voltage greater than 1.5 V or less than −1.5 V across both ends of the molecular junction device, the reversible electrically-controlled molecular switch device exhibits a low conductive state in a voltage range of −0.9 V to 0.9 V and a high conductive state in a voltage of greater than 1.5 V or less than −1.5 V at a temperature of 160 to 220 K when the reversible electrically-controlled molecular switch device comprises the diarylethene compound of Formula I-1 or Formula I-2.

8. A reversible temperature-controlled molecular switch device comprising the diarylethene-graphene molecular junction device of claim 2 , wherein when the reversible temperature-controlled molecular switch device comprises the diarylethene compound of Formula I-1 or I-2, the reversible temperature-controlled molecular switch device exhibits a low conductive state at a temperature below 160 K, and exhibits a high conductive state at a temperature above 220 K.

Assignees

• Univ Beijing

Inventors

• Guo Xuefeng
• Jia Chuancheng
• Xin Na
• Chen Hongliang
• Li Mingliang
• Qu Dahui

Classifications

• C07F15/0046

  Ruthenium compounds · CPC title

• C07C245/08

  with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene · CPC title

• G02F1/1333

  Constructional arrangements; {Manufacturing methods}(G02F1/135, G02F1/136 take precedence) · CPC title

• C07D495/10

  Spiro-condensed systems · CPC title

• C09K9/02

  Organic tenebrescent materials · CPC title