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Chemistry. 2014 Dec 15;20(51):16980-6. doi: 10.1002/chem.201404996. Epub 2014 Oct 22.

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

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College of Chemistry and Chemical Engineering, Central South University, Changsha, Hunan 410083 (P.R. China).


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.


donor-acceptor systems; hydrogen bonds; polymers; self-assembly; supramolecular chemistry


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