2016
DOI: 10.1021/acs.joc.6b01115
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A Shape-Persistent Cryptand for Capturing Polycyclic Aromatic Hydrocarbons

Abstract: A shape-persistent cryptand 1, containing two face-to-face oriented electron-deficient 2,4,6-triphenyl-1,3,5-triazine units separated by approximately 7 Å, and bridged by two rigid 1,8-naphthyridine linkers and a pentaethylene oxide loop, is created for capturing polycyclic aromatic hydrocarbons. Cryptand 1 formed 1:1 complexes with PAH guest molecules, such as phenanthrene (6), anthracene (7), pyrene (8), triphenylene (9), and tetraphene (10). The single-crystal structure of complex 6⊂1 revealed that 6 was in… Show more

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Cited by 12 publications
(9 citation statements)
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“…(iv) More complex systems with confined cavities can be achieved by enhancing the nuclearity of the adduct, e.g., by using tri-or tetra-amine ligands. These perspectives illustrate that this class of molecules could constitute an interesting alternative to Stoddart's X-boxes and -cages, 30,31 Peinador's and Fujita's palladium and platinum-based metallacycles and -cages, 32,33 Severin's and Iwasawa's oligonuclear boron cages, 23,34 among others, 35,36 all of which have shown high selectivity for the inclusion of large PAHs.…”
Section: Introductionmentioning
confidence: 96%
“…(iv) More complex systems with confined cavities can be achieved by enhancing the nuclearity of the adduct, e.g., by using tri-or tetra-amine ligands. These perspectives illustrate that this class of molecules could constitute an interesting alternative to Stoddart's X-boxes and -cages, 30,31 Peinador's and Fujita's palladium and platinum-based metallacycles and -cages, 32,33 Severin's and Iwasawa's oligonuclear boron cages, 23,34 among others, 35,36 all of which have shown high selectivity for the inclusion of large PAHs.…”
Section: Introductionmentioning
confidence: 96%
“…Cryptands exhibiting C 3 symmetry have been exciting synthetic targets, due to their high ability to form stable “host–guest” supramolecular assemblies (i.e., as result of the macrobicyclic effect [ 1 ]) either with ions (cations and anions) [ 2 , 3 , 4 ] or neutral organic molecules [ 5 , 6 , 7 , 8 , 9 ]. Many aromatic tripodand units were employed to access this type of cryptand.…”
Section: Introductionmentioning
confidence: 99%
“…Cryptands with C 3 -symmetric aromatic reference groups are exciting targets, on the one hand due to the challenges encountered in their synthesis and on the other due to their ability (macrobicyclic effect [ 1 ]) to form supramolecular assemblies with cations, anions or neutral guests, e.g., aromatic molecules [ 2 6 ]. The supramolecular architectures involving cryptands (including metallomacrocycles) and aromatic guests are targeted for investigations of aromatic–aromatic contacts [ 7 8 ] and for various applications in molecular electronics [ 9 10 ].…”
Section: Introductionmentioning
confidence: 99%
“…The synthesis of cryptands with C 3 symmetry by peculiar reactions (acetylenic coupling [ 16 18 ], CuAAC [ 19 22 ], double or triple bond metathesis [ 23 25 ], aromatic nucleophilic substitutions [ 26 33 ], or via the amplification of a cryptand belonging to DCC libraries [ 2 , 25 , 34 35 ]) allowed accessing of more sophisticated architectures. In a previous work [ 32 ] we reported the formation of a host–guest complex between a cryptand having pyridine units in the bridges and 1,3,5-triphenylbenzene caps ( 1 , Fig.…”
Section: Introductionmentioning
confidence: 99%