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Functionalized 3,3′,5,5′‐Tetraaryl‐1,1′‐Biphenyls: Novel Platforms for Molecular Receptors
Author(s) -
Welti Roger,
Abel Yvonne,
Gramlich Volker,
Diederich François
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390055
Subject(s) - chemistry , biphenyl , supramolecular chemistry , proton nmr , solvent , halide , suzuki reaction , stereochemistry , combinatorial chemistry , molecule , organic chemistry , aryl , alkyl
This paper describes the development of novel aromatic platforms for supramolecular construction. By the Suzuki cross‐coupling protocol, a variety of functionalized m‐ terphenyl derivatives were prepared ( Schemes 1–4 ). Macrolactamization of bis(ammonium salt) ( S,S )‐ 6 with bis(acyl halide) 7 afforded the macrocyclic receptor ( S,S )‐ 2 ( Scheme 1 ), which was shown by 1 H‐NMR titration studies to form ‘nesting' complexes of moderate stability ( K a between 130 and 290 M −1 , 300 K) with octyl glucosides 13 – 15 ( Fig. 2 ) in the noncompetitive solvent CDCl 3 . Suzuki cross‐coupling starting from 3,3′,5,5′‐tetrabromo‐1,1′‐biphenyl provided access to a novel series of extended aromatic platforms ( Scheme 5 ) for cleft‐type ( Fig. 1 ) and macrotricyclic receptors such as ( S,S,S,S )‐ 1 . Although mass‐spectral evidence for the formation of ( S,S,S,S )‐ 1 by macrolactamization between the two functionalized 3,3′,5,5′‐tetraaryl‐1,1′‐biphenyl derivatives ( S,S )‐ 33 and 36 was obtained, the 1 H‐ and 13 C‐NMR spectra of purified material remained rather inconclusive with respect to both purity and constitution. The versatile access to the novel, differentially functionalized 3,3′,5,5′‐tetrabromo‐1,1′‐biphenyl platforms should ensure their wide use in future supramolecular construction.