Hamilton-receptor

Figure 6.7 Illustration of multipoint hydrogen bonding based self-assembly (a) hydrogen bond formation between barbituric acid functionalized gold nanoparticles and Hamilton receptor functionalized block copolymers and (b) selective deposition of nanoparticles on a microphase-separated block copolymer film. Reprinted with permission fi om Binder et al. (2005). Copyright 2005 American Chemical Society.

Often designated briefly as Hamilton receptor , this barbiturate receptor niche (Fig. 6.12) consists of an isophthaloyl spacer flanked by two acylated 2,6-diaminopyridine moieties. Macrocyclisation with a rigid diphenylmethane unit generates a non-collapsing host cavity suitable for selective complexation of barbiturate guest molecules via formation of six hydrogen bonds. 

Fig. 6.12 Macrocyclic Hamilton receptor for barbiturate guest molecules (left-hand side). A non-cyclic Hamilton host compound with...

Fig. 6.13 POPAM dendrimer with peripheral Hamilton receptor niches (red) and docking of barbiturate guest molecules (green schematic)...

Jan-Frederik Gnichwitz, Mateusz Wielopolski, Kristine Hartnagel, Uwe Hartnagel, Dirk M. Guldi, Andreas Hirsch. Cooperativity and Tunable Excited State Deactivation Modular Self-Assembly of Depsipeptide Dendrons on a Hamilton Receptor Modified Porphyrin Platform. J. Am. Chem. Soc. 2008, 130, 8491. 

Fig. 41 Formation of helices and fibers from low molecular weight building blocks. The association takes place via the Hamilton receptor/cyamuate interaction. Reprinted with permission from [150]...

Scheme 1 Thymine/triazine and Hamilton receptor/barbituric acid interactions with association constants of 800 and 3 x 10 respectively [42]...

Fig. 2 Classification of supramolecular building blocks functionalized with hydrogen-bonding groups (HBGs) and a few examples of self-complementary and heterocomplementary binding motifs. BTA benzene-1,3,5-tricarboxyamide, UPy ureidopyrimidinone, DATdiamino triazine. Thy thymine, Napy 2,7-diaminonaphtyriine, Ba barbituric acid, HR hamilton receptor...

Binder et al employed two different sets of complementary hydrogen-bonding motifs to cormect phase-separating poly(iso-butylene) and poly(etherketone) in the bulk. The telechelic polymers were synthesized with both sets of hydrogen-bond motifs appended to their respective chain ends, and all polymers were able to yield hydrogen-bonded block copolymers capable of microphase separation. The strongly botmd Hamilton receptor motif (Ka=3 X 1stabilized the material up to 230 ° C, beyond which macrophase separation was observed. 

Scheme 9.4 Route to hydrogen-bonded polymers by combining ROMP and azide/alkyne click chemistry, (a) Direct polymerization approach [13, 17], ONBEs with thymine and Hamilton-receptor functionalities, 22a and b via azide/alkyne click reaction, followed by polymerization...

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