Pyrene-1,3,6,8-tetrone Quinones for Infrared Absorption
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Solution Overview
Problem
Current organic molecules fail to efficiently conduct electrical charges and excitons while absorbing the entire solar spectrum, including infrared, due to limited stability and absorption capabilities at room temperature.
Innovation Solution
Development of new higher homologs of 2,7-dihydro-pyrene-1,3,6,8-tetrones with enolizable 1,3-dione functions, capable of forming mesogenic phases and absorbing longer wavelengths, synthesized using cesium or rubidium hydroxide to enhance solubility and absorption properties.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Use of energy by moving object
If conventional organic molecules are used, then the structure is simple and synthesis is easy, but the absorption capability in infrared and solar spectrum is insufficient
Solution Approach 1:
The molecule is divided into distinct functional segments: a rigid disc-shaped core (pyrene or peropyrene skeleton) providing structural stability and mesogenic properties, and flexible side chains (alkyl or aryl groups) providing solubility and conformational flexibility. This segmentation allows each part to optimize its specific function while working together to achieve broad solar spectrum absorption including infrared regions.
Solution Approach 2:
The invention creates composite molecular structures combining multiple functional motifs within a single molecule: the rigid disc core provides charge transport and mesogenic phase formation, while the flexible side chains provide solubility and molecular packing. This composite approach within molecules enables simultaneous achievement of absorption, charge conduction, and self-assembly properties that single-functional molecules cannot provide.
2Use of energy by moving object
If molecules with high absorption coefficient in infrared are developed, then solar spectrum absorption is improved, but stability at room temperature deteriorates
Solution Approach 1:
Different parts of the molecule have different structural qualities optimized for specific functions: the rigid disc core (pyrene or peropyrene skeleton with conjugated double bonds) provides high infrared absorption and charge transport capability, while the flexible side chains (alkyl or aryl groups) provide thermal stability and prevent aggregation at room temperature. This local differentiation of structural quality allows the molecule to simultaneously achieve high absorption and stability.
3Reliability
If columnar liquid crystal forming capability is achieved, then charge and exciton conduction is improved, but solubility in organic solvents deteriorates
Solution Approach 1:
The molecule exhibits dynamic conformational flexibility through the flexible side chains that can adapt their arrangement based on environmental conditions. In solution, the flexible side chains provide solubility by preventing crystallization, while in the solid state or at higher concentrations, the rigid disc cores self-assemble into columnar liquid crystal phases for efficient charge conduction. This dynamic adaptability allows the molecule to switch between solubility and self-assembly modes as needed.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
These compounds exhibit improved solubility and absorption across the visible and infrared spectrum, making them suitable for use in organic photovoltaic cells as charge and exciton conductors, increasing the diffusion length of excitons and mobility of charges.
Implementation Method 1
The absorption maximum of these new compounds increases with the value of p and the homologs for which p is greater than 3 show absorption in the infrared
Implementation Method 2
The keto-enol isomerism also allows the introduction of one or two substituents per molecule, for example by esterification or etherification of the enol form
Implementation Method 3
molecules having the shape of rigid discs with flexible side chains have been found to form columnar mesogenic phases potentially very interesting as charge and/or exciton conductors
Implementation Method 4
The synthesis of quinones of higher order (n = 1 to 5) can be done by cyclization of precursors of formula (III)
Data Source
Figure 1
AI summary
The invention relates to quinones of formula (Ia) or (Ib), in which Formula (Ia) and Formula (Ib) R1 and R2 each independently represent - a hydrogen atom, - a C1-3O alkyl group in which one or more -CH2- linkages, apart from the attachment linkage, may be replaced by an oxygen atom, a sulphur atom, or an NH, N(C1-4 alkyl) or C=O group, and which is optionally substituted, or - an optionally substituted C6-10 aryl or C4-1O heteroaryl group, each R3 independently represents - a hydrogen atom, a linear or branched C1-3O alkyl group, in which one or more -CH2- linkages may be replaced by an oxygen atom, a sulphur atom, or an NH, N(C1-4 alkyl) or C=O group, and which is optionally substituted, or - a C6-1O aryl, C4-1O heteroaryl, (C6-10 aryl)carbonyl, or (C4-10 heteroaryl)carbonyl group, each of these groups optionally being substituted, and n is an integer between 1 and 5 inclusive. The invention also relates to a method for synthesizing these quinones and also to the use of these quinones as dyes, in particular dichroic dyes, and/or as charge carriers and/or exciton carriers in photoelectric devices.