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An AAA–DDD Triply Hydrogen‐Bonded Complex Easily Accessible for Supramolecular Polymers
Author(s) -
Han YiFei,
Chen WenQiang,
Wang HongBo,
Yuan YingXue,
Wu NaNa,
Song XiangZhi,
Yang Lan
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404996
Subject(s) - hydrogen bond , supramolecular chemistry , chemistry , acceptor , pyridine , annulation , hydrogen , chloroform , polymer , titration , polymer chemistry , crystallography , photochemistry , combinatorial chemistry , inorganic chemistry , molecule , organic chemistry , crystal structure , catalysis , physics , condensed matter physics
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 Friedländer annulation reaction. The association constant determined by fluorescence titration in chloroform at room temperature is 2.09×10 7 M −1 . 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.