Fused Ring Indeno Compounds for Photochromic Synthesis

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Solution Overview

Problem

Current methods for synthesizing fused ring indeno compounds, used as intermediates for photochromic materials, are limited by the types of groups that can be introduced at specific ring positions, leading to reduced product yields and higher costs, particularly for photochromic indeno-fused naphthopyrans.

Innovation Solution

Development of a fused ring indeno compound represented by Formula (I-A), which allows for the introduction of various groups at different ring positions through a specific synthetic scheme, enabling the preparation of photochromic compounds with enhanced flexibility and reduced costs.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If the Stobbe reaction route is used to synthesize fused ring indeno compounds, then the basic synthesis can be achieved, but the types of groups that can be introduced at specific ring positions are limited and product yields are reduced

Engineering Contradiction:
Improvetypes of groups that can be introducedVSAvoidproduct yields
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

The patent changes the synthetic route from the traditional Stobbe reaction to a new methodology that uses different reaction parameters and conditions, enabling the introduction of diverse groups at ring positions while maintaining or improving product yields. This parameter change in the synthesis approach resolves the contradiction between versatility and productivity.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If additional synthetic steps are taken to introduce groups at various ring positions, then group diversity can be achieved, but synthesis costs increase due to additional isolation steps

Engineering Contradiction:
Improvegroup introduction capabilityVSAvoidsynthesis costs
Core Design Contradiction:
Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

The patent incorporates group introduction capabilities directly into the main synthetic pathway, performing the group introduction action preliminarily during the core synthesis steps rather than requiring separate additional steps. This preliminary action eliminates the need for extra isolation steps, thereby reducing synthesis costs while maintaining group diversity capability.

Inventive Principle:
Principle #10Preliminary action

3Ease of manufacture

If conventional synthesis methods are used for photochromic indeno-fused naphthopyrans, then synthesis can be performed, but the cost is expensive

Engineering Contradiction:
Improvesynthesis costVSAvoidphotochromic material quality
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent develops a new synthetic pathway that replicates the desired photochromic indeno-fused naphthopyrans through an alternative route, copying the final product structure but achieving it through different, more cost-effective intermediate steps. This copying approach maintains product quality while reducing synthesis costs.

Inventive Principle:
Principle #26Copying

Data Source

PatentEP3071551B1Fused ring indeno compounds for preparation of photochromic compounds
Publication Date: 2021.08.25 TRANSITIONS OPTICAL INC
  • EP3071551B1 patent drawingFigure 1
  • EP3071551B1 patent drawingFigure 2
  • EP3071551B1 patent drawingFigure 3

AI summary

The present invention relates to intermediate compounds represented by the following Formula (l-A), The intermediate compounds of the present invention, such as represented by Formula (I-A), can be used to prepare photochromic compounds, such as photochromic fused ring indenopyran compounds, including but not limited to photochromic fused ring indeno-naphtho-pyran compounds.