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Binding of alpha,omega-alkyldiammonium ions by cucurbit[n]urils in the gas phase

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Title
Binding of alpha,omega-alkyldiammonium ions by cucurbit[n]urils in the gas phase
Author(s)
Yang, F; Jones, CA; Selvapalam, N; Young Ho Ko; Ki Moon Kim; Dearden, DV
Publication Date
2014-09
Journal
SUPRAMOLECULAR CHEMISTRY, v.26, no.9, pp.684 - 691
Publisher
TAYLOR & FRANCIS LTD
Abstract
We investigated gas-phase complexes of a,v-n-alkyldiammonium ions with cucurbit[5]uril (CB[5]), decamethylcucurbit[5] uril (mc5), penta(cyclohexyl)cucurbit[5]uril (CB*[5]), hexa(cyclohexyl)cucurbit[6]uril (CB*[6]), cucurbit[7]uril (CB[7]) and cucurbit[8]uril (CB[8]) using electrospray Fourier transform ion cyclotron resonance mass spectrometry and collisioninduced dissociation techniques. The five-membered cucurbit[n]urils (CB[n]s) form singly charged 1:1 and doubly charged 2:1 diamine:CB[n] complexes. All dissociate via loss of neutral a,v-n-alkyldiamine with only weak dependence of dissociation thresholds on chain length. For a given diamine, threshold energies are in the order CB[5] , mc5 , CB*[5]. This is consistent with guest hydrogen bonding on the portals of the CB[5]s with no threading into the host’s interior. The n $ 6 CB[n]s form 1:1 complexes with doubly protonated a,v-n-alkyldiamines. These collisionally dissociate via four channels: loss of singly protonated a,v-n-alkyldiammonium; fragmentation of the CB[n] cage; loss of neutral a,v-nalkyldiamine and fragmentation of the a,v-n-alkyldiamine. The dissociation threshold energies and branching ratios exhibit strong dependence on the length of the a,v-n-alkyldiamine and the size of the CB[n]. The data suggest that the optimum a, v-n-alkyldiamine length for binding CB*[6] is three to four methylene groups; for CB[7], four to five methylene groups and for CB[8], five to six methylene groups, indicating an increasing tendency for the guest to span the host cavity diagonally as the size of the CB[n] increases.
URI
https://pr.ibs.re.kr/handle/8788114/923
ISSN
1061-0278
Appears in Collections:
Center for Self-assembly and Complexity(복잡계 자기조립 연구단) > Journal Papers (저널논문)
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