Naphthodithiophene Diimide Based Chiral π-Conjugated Nanopillar Molecules.

Angew Chem Int Ed Engl

Department of Chemistry, College of Chemistry and Chemical Engineering, MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, Xiamen University, Xiamen, 361005, China.

Published: November 2021

AI Article Synopsis

  • The synthesis of [4]cyclonaphthodithiophene diimides (C-NDTIs) is accomplished through a unique electrochemical-oxidation macrocyclization method, creating a stable pillar structure.
  • The resulting molecules exhibit desirable electronic and optical properties, including strong near-infrared light absorption and stable chirality due to their fixed NDTI unit orientations.
  • Their ability to stack efficiently in two-dimensional arrangements makes [4]C-NDTIs promising candidates for creating multifunctional organic materials that could emulate natural photosynthesis.

Article Abstract

The synthesis, structures, and properties of [4]cyclonaphthodithiophene diimides ([4]C-NDTIs) are described. NDTIs as important n-type building blocks were catenated in the α-positions of thiophene rings via an unusual electrochemical-oxidation-promoted macrocyclization route. The thiophene-thiophene junction in [4]C-NDTIs results in an ideal pillar shape. This interesting topology, along with appealing electronic and optical properties inherited from the NDTI units, endows the [4]C-NDTIs with both near-infrared (NIR) light absorptions, strong excitonic coupling, and tight encapsulation of C . Stable orientations of the NDTI units in the nanopillars lead to stable inherent chirality, which enables detailed circular dichroism studies on the impact of isomeric structures on π-conjugation. Remarkably, the [4]C-NDTIs maintain the strong π-π stacking abilities of NDTI units and thus adopt two-dimensional (2D) lattice arrays at the molecular level. These nanopillar molecules have great potential to mimic natural photosynthetic systems for the development of multifunctional organic materials.

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Source
http://dx.doi.org/10.1002/anie.202107893DOI Listing

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