Supramolecular polymer chemistry: Self-assembling dendrimers using the DDA·AAD (GC-like) hydrogen bonding motif

Yuguo Ma; Sergei V. Kolotuchin; Steven C. Zimmerman

doi:10.1021/ja0202006

Supramolecular polymer chemistry: Self-assembling dendrimers using the DDA·AAD (GC-like) hydrogen bonding motif

Yuguo Ma, Sergei V. Kolotuchin, Steven C. Zimmerman

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185 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	13757-13769
Number of pages	13
Journal	Journal of the American Chemical Society
Volume	124
Issue number	46
DOIs	https://doi.org/10.1021/ja0202006
State	Published - 20 Nov 2002
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja0202006

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title = "Supramolecular polymer chemistry: Self-assembling dendrimers using the DDA·AAD (GC-like) hydrogen bonding motif",

abstract = "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) Fr{\'e}chet-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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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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Supramolecular polymer chemistry: Self-assembling dendrimers using the DDA·AAD (GC-like) hydrogen bonding motif

Abstract

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