Chiral rodlike platinum complexes, double helical chains, and potential asymmetric hydrogenation ligand based on "linear" building blocks: 1,8,9,16-Tetrahydroxytetraphenylene and 1,8,9,16-tetrakis(diphenylphosphino) tetraphenylene

Hai Yan Peng, Chi Keung Lam, Thomas C.W. Mak, Zongwei CAI, Wai Tang Ma, Yu Xue Li, Henry N.C. Wong*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

98 Citations (Scopus)

Abstract

This paper is concerned with the synthesis of 1,8,9,16- tetrahydroxytetraphenylene (3a) via copper-(II)-mediated oxidative coupling, its resolution to optical antipodes, and its conversion to 1,8,9,16- tetrakis(diphenylphosphino)tetraphenylene (3b). On the basis of these chiral "linear" building blocks, three rodlike chiral complexes, triblock (R,R,R,R)-17 and (S,S,S,S)-20 and pentablock (R,R,R,R,R,R,R,R)-22, were constructed. As a hydrogen bond donor, racemic and optically active 3a was allowed to assemble with linear acceptors to afford highly ordered structures. A 1:1 adduct of 4,4′-bipyridyl and (±)-3a exists in a dimeric form of 3a linked by 4,4′-bipyridyl through hydrogen bonds. Pyrazine serves as a short linker between achiral parallel chains each formed by (±)-3a, while self-assembly of homochiral 3a into alternate parallel chains occurs in the adduct of 5,5′-dipyrimidine with (±)-3a. Self-assembly of (S,S)-3a or (R,R)-3a with 4,4′-dipyridyl yielded a packing of chiral double helical chains formed by chiral tetrol 3a molecules. A novel chiral ligand, (S,S)-23, derived from 3a was used in the asymmetric catalytic hydrogenation of α-acetamidocinnamate, yielding up to 99.0% ee and 100% conversion.

Original languageEnglish
Pages (from-to)9603-9611
Number of pages9
JournalJournal of the American Chemical Society
Volume127
Issue number26
DOIs
Publication statusPublished - 6 Jul 2005

Scopus Subject Areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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