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Asymmetric Core-Expanded BOPYOs: Facile Synthesis and Optical Properties.

Peng Su1, Liu Wen1, Yongzhu Zhou2,3

  • 1College of Materials and Chemical Engineering, Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, China Three Gorges University, No. 8 Daxue Road, Yichang, 443002, Hubei, P. R. China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 30, 2022
PubMed
Summary

Researchers developed novel seven-membered boron complexes, borondifluoride-(Z)-1,3-di(1H-pyrrol-2-yl)but-2-en-1-one (BOPYO), and their derivatives. These compounds exhibit tunable properties and potential as near-infrared (NIR) dyes.

Keywords:
BOPYON, O-BF2 complexesNIR emissiondensity functional calculationsseven-membered rings

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • N,O-bidentate BF2 complexes with five- and six-membered rings are well-studied.
  • Seven-membered N,O-boron complexes remain an underexplored area in chemical research.

Purpose of the Study:

  • To develop novel seven-membered N,O-boron complexes.
  • To explore the synthesis and reactivity of core-expanded borondifluoride-(Z)-1,3-di(1H-pyrrol-2-yl)but-2-en-1-one (BOPYO).
  • To create new near-infrared (NIR) dyes with tunable photophysical properties.

Main Methods:

  • BF3·OEt2-induced self-condensation and coordination reactions.
  • Experimental characterization and computational elucidation.
  • Reactions with various aldehydes to form conjugated BOPYOs.
  • Synthesis of a dimethylamino-substituted BOPYO derivative.

Main Results:

  • Successful development of the parent asymmetric core-expanded borondifluoride-(Z)-1,3-di(1H-pyrrol-2-yl)but-2-en-1-one (BOPYO).
  • Demonstrated reactivity of BOPYO with diverse aldehydes, yielding a series of conjugated BOPYOs.
  • A novel NIR dye derivative exhibiting acid-responsive, favorable photophysical properties via intramolecular charge transfer.

Conclusions:

  • Established a synthetic route to seven-membered N,O-boron complexes.
  • BOPYO serves as a versatile platform for creating conjugated systems.
  • The developed BOPYO derivative shows promise as an acid-responsive NIR dye.