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Synthesis and Self‐Association of Double‐Helical AADD Arrays
Author(s) -
Mudraboyina Bhanu P.,
Wisner James A.
Publication year - 2012
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.201201668
Subject(s) - dimer , chemistry , hydrogen bond , range (aeronautics) , stereochemistry , crystallography , molecule , materials science , organic chemistry , composite material
The design and syntheses of four self‐complementary oligomers that contain an underlying AADD hydrogen bond sequence are presented, and their self‐association was examined in the solution and solid state. The molecular recognition between the two strands is highly sensitive to substitutions of their component heterocycles. Substitution with electron‐donating and ‐withdrawing groups and the influence of preorganization has a large effect on the overall stabilities of the complexes studied. In particular, a wide range (>10 5 M −1 ) of stabilities with respect to substitutions at various positions in the AADD oligomers was demonstrated. In the most extreme case, the dimerization constant measured ( K dimer ≥4.5×10 7 M −1 ) is comparable to the most stable homodimers of neutral AADD arrays reported to date.