Self-assembly of rectangular shape-persistent diazaborole-linked macrocycles

  • Sanjaya D. Lokugama
  • Nicholas A. Garcia
  • Chamila P. Manankandayalage
  • Thao N. Nguyen
  • Janaka P. Abeysinghe
  • Dustin E. GrossEmail author
Original Article


Diazaboroles have become of recent interest in the area of organic materials. In this work we have synthesized arylene ethynylene macrocycles using diazaborole formation as the key chain-linking step. Specifically, bis(benzene-1,2-diamine) monomers were successfully condensed with 1,4-phenylenediboronic acid, which resulted in novel diazaborole-linked macrocycles through the formation of four diazaborole linkages. The new macrocycles were characterized by NMR spectroscopy, MALDI mass spectrometry, and computational calculations. These macrocycles may serve as model compounds for future diazaborole-based covalent organic frameworks.


Macrocycles Dynamic covalent chemistry Diazaboroles Self-assembly Boronic acids 



This work was supported in part by the Welch Foundation [Grant x-0011] and start-up funding from Sam Houston State University. Acknowledgment is made to the Donors of the American Chemical Society Petroleum Research Fund for partial support of this research.

Supplementary material

10847_2018_878_MOESM1_ESM.doc (7.4 mb)
Supplementary material 1 (DOC 7554 KB)


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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of ChemistrySam Houston State UniversityHuntsvilleUSA

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