2015
DOI: 10.1021/jacs.5b06590
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Concerted Halogen-Bonded Networks with N-Alkyl Ammonium Resorcinarene Bromides: From Dimeric Dumbbell to Capsular Architectures

Abstract: N-Alkyl ammonium resorcinarene bromides and 1,4-diiodooctafluorobutane via multiple intermolecular halogen bonds (XB) form different exotic supramolecular architectures through subtle changes of the upper rim substituents. Dimeric dumbbell-like assembly with encapsulated guest molecules is generated with N-benzyl substituents. The N-hexyl groups engender an XB-induced polymeric pseudocapsule and an XB-induced dimeric capsule with entrapped 1,4-dioxane guest molecules. The N-propyl and N-cyclohexyl groups gener… Show more

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Cited by 34 publications
(44 citation statements)
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“…Overall, macrocycles are interesting compounds for supramolecular chemistry as besides having a large structural variation, they are capable of molecular recognition and complex formation . The particular resorcinarene XB acceptor was chosen based on previous research, which shows that it acts as a sufficient XB acceptor both in solid and liquid state . Self‐assembly of the selected compounds leads into spherical complexes held together by the interaction between the XB donor iodine and XB acceptor bromide.…”
Section: Methodsmentioning
confidence: 99%
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“…Overall, macrocycles are interesting compounds for supramolecular chemistry as besides having a large structural variation, they are capable of molecular recognition and complex formation . The particular resorcinarene XB acceptor was chosen based on previous research, which shows that it acts as a sufficient XB acceptor both in solid and liquid state . Self‐assembly of the selected compounds leads into spherical complexes held together by the interaction between the XB donor iodine and XB acceptor bromide.…”
Section: Methodsmentioning
confidence: 99%
“…[12] For example, haloarenes are known to be effective in this kind of strengthening. [13] Halogen bonding has been studied widely with cavitands [14][15][16][17] and in macromolecular systems. [18][19][20][21][22][23][24][25][26] With the cavitands, focus in halogen bonding has been among forming capsules, [14] networks, [16] and ribbons.…”
mentioning
confidence: 99%
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“…6 Despite the work already performed, there remains a need to investigate small biomolecular systems where XBs and non-conventional HBs, such as C-H … O, are simultaneously present, as the latter interactions are ubiquitous in many small molecule crystal structures 24,25 and advantageously used for enhancing the efficiency of weak base pairing in DNA. [26][27][28][29][30][31][32][33] Due to our continuing interest in the potential of pyrimidine nucleobases for crystal engineering strategies underpinned by multiple HBs [34][35][36][37][38][39][40][41][42][43][44][45] and our involvement in studies of systems exhibiting halogen bonding via alternative donors (halogen atom not polarized by fluorine) and acceptors (such as anions), [46][47][48][49][50][51][52][53][54][55][56][57][58][59] we were interested in search for systems that could be used to investigate the role of concurrent XBs and non-conventional HBs in the control of sequence, structure and flexibility of DNA halogenated within the natural tract. For this purpose, 5-halogenated derivatives (DMXU; X=F, Cl, Br, I) of N,N-1,3-dimethyluracil (DMHU) and their mixed cocrystals are ideal candidates because of several advantageous properties.…”
Section: Introductionmentioning
confidence: 99%
“…Reports have shown the N ‐alkyl ammonium resorcinarene salts to be suitable receptors for a variety of neutral guests and recently anions through several simultaneous weak interactions utilizing the electron‐rich resorcinarene cavity and the hydrogen bonded cation‐anion seam. Furthermore, the four spatially fixed anions can act as halogen‐bond acceptors, and, through concerted halogen bonds, result in molecular architectures with guest binding properties such as deep cavity cavitands, capsular, and dumbbell‐like dimeric assemblies …”
Section: Introductionmentioning
confidence: 99%