TY - JOUR
T1 - Supramolecular polymer chemistry
T2 - Self-assembling dendrimers using the DDA·AAD (GC-like) hydrogen bonding motif
AU - Ma, Yuguo
AU - Kolotuchin, Sergei V.
AU - Zimmerman, Steven C.
PY - 2002/11/20
Y1 - 2002/11/20
N2 - Heterocyclic unit 2 containing complementary donor-donor-acceptor (DDA) and acceptor-acceptor-donor (AAD) hydrogen bonding arrays at an angle of about 60° was designed to self-assemble into a hexamer. To investigate whether this unit could self-assemble dendrimers, the 2,8-diamino-2-N-ethylpyrimido-(4,5-b)(1,8)naphthyridine-3H-4-one subunit was synthesized with a first (2a), second (2b), and third generation (2c) Fréchet-type dendron attached to the 8-amino group. The synthesis of 2a-c was accomplished in 11 steps beginning with 2,6-diaminopyridine and the corresponding dendron bromide. Studies using 1H NMR, size exclusion chromatography (SEC), and dynamic light scattering (DLS) support the cooperative formation of cyclic hexamers in apolar solvents. The stability of the self-assembled dendrimers is dependent on the size of the attached dendron, and mixing studies with 2a-c indicate their usefulness in constructing dynamic combinatorial libraries.
AB - Heterocyclic unit 2 containing complementary donor-donor-acceptor (DDA) and acceptor-acceptor-donor (AAD) hydrogen bonding arrays at an angle of about 60° was designed to self-assemble into a hexamer. To investigate whether this unit could self-assemble dendrimers, the 2,8-diamino-2-N-ethylpyrimido-(4,5-b)(1,8)naphthyridine-3H-4-one subunit was synthesized with a first (2a), second (2b), and third generation (2c) Fréchet-type dendron attached to the 8-amino group. The synthesis of 2a-c was accomplished in 11 steps beginning with 2,6-diaminopyridine and the corresponding dendron bromide. Studies using 1H NMR, size exclusion chromatography (SEC), and dynamic light scattering (DLS) support the cooperative formation of cyclic hexamers in apolar solvents. The stability of the self-assembled dendrimers is dependent on the size of the attached dendron, and mixing studies with 2a-c indicate their usefulness in constructing dynamic combinatorial libraries.
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U2 - 10.1021/ja0202006
DO - 10.1021/ja0202006
M3 - Article
C2 - 12431106
AN - SCOPUS:0037146006
SN - 0002-7863
VL - 124
SP - 13757
EP - 13769
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 46
ER -