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Role of exciton delocalization in chiroptical properties of benzothiadiazole carbon nanohoops. | LitMetric

AI Article Synopsis

  • Developing chiral organic materials with strong optical responses is essential for applications like enantioselective sensing and anti-counterfeiting technology.
  • This study synthesizes two novel chiral macrocycles combining a unique structure and fluorescent properties, allowing a detailed exploration of their electronic behaviors.
  • The researchers established a key structure-property relationship that could guide future designs of materials with enhanced circularly polarized light capabilities.

Article Abstract

Development of chiral organic materials with a strong chiroptical response is crucial to advance technologies based on circularly polarized luminescence, enantioselective sensing, or unique optical signatures in anti-counterfeiting. The progress in the field is hampered by the lack of structure-property relationships that would help designing new chiral molecules. Here, we address this challenge by synthesis and investigation of two chiral macrocycles that integrate in their structure a pseudo-meta [2.2]paracyclophane with planar chirality and a highly fluorescent benzothiadiazole. Both compounds display remarkably red-shifted fluorescence with high quantum yields and large Stokes shifts. They differ in the extent of π-electron conjugation that allowed, for the first time, systematic examination of the effect of exciton delocalization on the absorption and luminescence of circularly polarized light. By a combination of steady-state spectroscopy and quantum chemical calculations, we constructed a unique structure-property relationship offering critical insights that will aid and abet the development of robust design guidelines for materials with strong electronic circular dichroism or circularly polarized luminescence of exceptional brightness.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11659672PMC
http://dx.doi.org/10.1039/d4sc07333aDOI Listing

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