An AAA-DDD triply hydrogen-bonded complex easily accessible for supramolecular polymers

Yi Fei Han, Wen Qiang Chen, Hong Bo Wang*, Ying Xue Yuan, Na Na Wu, Xiang Zhi Song, Lan Yang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

For a complementary hydrogen-bonded complex, when every hydrogen-bond acceptor is on one side and every hydrogen-bond donor is on the other, all secondary interactions are attractive and the complex is highly stable. AAA-DDD (A=acceptor, D=donor) is considered to be the most stable among triply hydrogen-bonded sequences. The easily synthesized and further derivatized AAA-DDD system is very desirable for hydrogen-bonded functional materials. In this case, AAA and DDD, starting from 4-methoxybenzaldehyde, were synthesized with the Hantzsch pyridine synthesis and Friedlnder annulation reaction. The association constant determined by fluorescence titration in chloroform at room temperature is 2.09107m1. The AAA and DDD components are not coplanar, but form a V shape in the solid state. Supramolecular polymers based on AAA-DDD triply hydrogen bonded have also been developed. This work may make AAA-DDD triply hydrogen-bonded sequences easily accessible for stimuli-responsive materials.

Original languageEnglish
Pages (from-to)16980-16986
Number of pages7
JournalChemistry - A European Journal
Volume20
Issue number51
DOIs
Publication statusPublished - 15 Dec 2014
Externally publishedYes

Keywords

  • Donor-Acceptor systems
  • Hydrogen bonds
  • Polymers
  • Self-Assembly
  • Supramolecular chemistry

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