Photoisomeric compounds and device comprising the same

Abstract

Disclosed are a series of photoisomeric compounds, preparation method therefor and device comprising the compounds. A photoisomeric compound-grephene 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 high reversibility and good reproducibility. The number of light-controlled switching cycles can exceed 10 4 , and the number of electrically-controlled switching cycles can reach about 10 5 or greater. The reversible molecular switch device remains stable within a period of more than one year. Flexible non-losable organic memory transistor devices and light-responsive organic transistor devices can be constructed using the series of photoisomeric compounds.

1 . A diarylethene compound, having any one of the following formulas: 
       
         
           
           
               
               
           
         
         wherein Cn 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 . A diarylethene-graphene molecular junction device, wherein the molecular junction device comprises any one of the diarylethene compound of  claim 1 , linked to a gap of a two-dimensional monolayer graphene having a nanogap array via an amide covalent bond. 
     
     
         3 . A reversible molecular switch device or a transistor device, wherein:
 (1) the reversible molecular switch device is a reversible light-controlled molecular switch device comprising the diarylethene-graphene molecular junction device of  claim 2 , 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 7  comprising the diarylethene-graphene molecular junction device of  claim 2  and a voltage generating means connected to the molecular junction device; wherein the voltage generating means is used to supply:
 (a) a voltage of 0.2 V to 1.5 V or a voltage of −0.2 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 0.2 V to 1.5 V or the voltage of −0.2 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 1 or Formula 2; and 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 Formulas 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 160 to 220 K when the reversible electrically-controlled molecular switch device comprises the diarylethene compound of Formula 1 or Formula 2; and 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 Formulas 1-4; or   (3) the reversible molecular switch device is a reversible temperature-controlled molecular switch device 7  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 1 or 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; and when the reversible temperature-controlled molecular switch device comprises a diarylethene compound of any of Formulas 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 any one of the diarylethene compound of  claim 1  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 - 18  (canceled) 
     
     
         19 . The diarylethene compound of  claim 1 , comprising any one of the following formulas: 
       
         
           
           
               
               
           
         
       
     
     
         20 . 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. 
     
     
         21 . The reversible molecular switch device or a transistor device of  claim 3 , wherein the reversible electrically-controlled molecular switch device comprises the diarylethene compound of Formula I-1, Formula I-2, Formula II-1, Formula II-2, Formula III-1 or Formula III-2. 
     
     
         22 . 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 Formula I-1, Formula I-2, Formula II-1, Formula II-2, Formula III-1 or Formula III-2. 
     
     
         23 . The reversible molecular switch device or a transistor device of  claim 3 , wherein the reversible temperature-controlled molecular switch device further comprises a temperature control means for providing the temperature-controlled molecular switch device with a temperature below 160 K or above 220 K, or a temperature below 100 K or above 300 K.