A chiral indolocarbazole foldamer displaying strong circular dichroism responsive to anion binding

Kim, Dan A; Kang, Philjae; Choi, Moon‐Gun; Jeong, Kyu Sung

doi:10.1039/c3cc45989f

Cited by 22 publications

(20 citation statements)

References 32 publications

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“…Two-armed host 27 (Figure 17) also forms strong C–H···X − hydrogen bonds, both in solution and in the solid state. [89] X-ray crystal structure determination of the 27 ·Cl − complex showed a short and highly linear C–H···Cl − contact. The hydrogen bonding interaction was also evident in solution by a large downfield shift of the core proton upon addition of anions.…”

Section: Charged Speciesmentioning

confidence: 99%

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Ion and Molecular Recognition Using Aryl–Ethynyl Scaffolding

Vonnegut

Tresca

Johnson

et al. 2015

Chemistry An Asian Journal

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The aryl–ethynyl linkage has been extensively employed in the construction of hosts for a variety of guests. Uses range from ion detection (e.g., of metal cations in the environment or industrial waste and of anions prevalent in nature), to molecular mimics for biological systems, and to applications targeting future safety issues (such as CO2 capture and indicators for the manufacture of chemical weapons). This Focus Review examines the utilization of the aryl–ethynyl linkage in engineering host molecules for a variety of different guests, and how the alkyne unit plays an integral part as both a rigid scaffolding section in host geometry design as well as a linker to allow conjugative communication between discrete π-electron systems.

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Section: Charged Speciesmentioning

confidence: 99%

“…[89] The addition of chiral methylene groups to a known indolocarbazole anion probe produced foldamer 37 with a strong helicity preference measured by CD in non-polar solvents. The chiral response of this probe is affected by both the solvent polarity and the presence of anions in solution.…”

Section: Emerging Areasmentioning

confidence: 99%

Ion and Molecular Recognition Using Aryl–Ethynyl Scaffolding

Vonnegut

Tresca

Johnson

et al. 2015

Chemistry An Asian Journal

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“…[20,21] Foldamers are an acyclic type of anion receptors folding around the anion due to multiple noncovalent interactions. [22][23][24] Although foldamers interact mainly via hydrogen bond interactions, recently, many foldamers with halogen and chalcogen bonds have been reported. [25,26] It has been found that the anion receptors with large halogens (I, Br) as acceptor site, interact more strongly with anions.…”

Section: Introductionmentioning

confidence: 99%

Anion receptors with 1,3,5‐triazacyclohexane and 1,4,7,10‐tetraazacyclododecane scaffolds

Valadbeigi

Ilbeigi

2020

J of Physical Organic Chem

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Fluoride, chloride, and bromide affinities of 1,3,5-triazacyclohexane (TACH) and 1,4,7,10-tetraazacyclododecane (Cyclen) were studied theoretically using ωB97XD and B3LYP functionals and 6-311++G(d,p) basis set. To enhance and modify the anion affinities of TACH and Cyclen, several anion receptors with-(CH 2) n OH and-(CH 2) n NH 2 (n = 1-3) substituents were designed and investigated. These anion receptors are attached to the halides (X −) via formation of NH … X and OH … X hydrogen bonds. The anion affinities calculated by ωB97XD were larger than those obtained by B3LYP indicating the dispersion contribution to the anion affinities. It was found that the anion affinities of these compounds depend on both the alkyl chain length and nature of the interaction, NH … X or OH … X. The ωB97XD-calculated fluoride affinities of TACH and Cyclen were 149.5 and 207.2 kJ mol −1 , respectively. By substitution of-(CH 2) n OH groups, anion receptors with F − affinities of 277 and 326 kJ mol −1 were obtained, which can be classified among the strongest organic anion receptors. The affinity of all TACH and Cyclen toward the halides was as F − > Cl − > Br − , while substitution of-(CH 2) 3 OH and-(CH 2) 3 NH 2 into Cyclen changed the trend to F − > Br − > Cl − .

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“…Foldamers are synthetic chain moleculesd esigned to manifest specific,o rdered conformations. [1][2][3][4][5][6][7][8][9][10][11] The eleganth igher-order structureso fp roteins and nucleic acids are attractive emulation targets in the foldamer designs. Although realizing sophisticated biomimeticf unctions with such synthetic systems are still challenging and far-fetched at this point, many foldamers are designed to serve as suitable models for studying biological systems of delicate nature and have provided useful insights into their intricate behavior and functions.…”

Section: Introductionmentioning

confidence: 99%

“…Foldamers are synthetic chain molecules designed to manifest specific, ordered conformations . The elegant higher‐order structures of proteins and nucleic acids are attractive emulation targets in the foldamer designs.…”

Section: Introductionmentioning

confidence: 99%

Helical Folding Competing with Unfolded Aggregation in Phenylene Ethynylene Foldamers

Luo

Zhu

Zhao

2016

Chemistry A European J

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The folding and aggregation behavior of a pair of oligo(phenylene ethynylene) (OPE) foldamers are investigated by means of UV/Vis absorption and circular dichroism spectroscopy. With identical OPE backbones, two foldamers, 1 with alkyl side groups and 2 with triethylene glycol side chains, manifest similar helical conformations in solutions in n-hexane and methanol, respectively. However, disparate and competing folding and aggregation processes are observed in alternative solvents. In cyclohexane, oligomer 1 initially adopts the helical conformation, but the self-aggregation of unfolded chains, as a minor component, gradually drives the folding-unfolding transition eventually to the unfolded aggregate state completely. In contrast, in aqueous solution (CH3 OH/H2 O) both folded and unfolded oligomer 2 appear to undergo self-association; aggregates of the folded chains are thermodynamically more stable. In solutions with a high H2 O content, self-aggregation among unfolded oligomers is kinetically favored; these oligomers very slowly transform into aggregates of helical structures with greater thermodynamic stability. The folded-unfolded conformational switch thus takes place with the free (nonaggregated) molecules, and the very slow folding transition is due to the low concentration of molecularly dispersed oligomers.

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A chiral indolocarbazole foldamer displaying strong circular dichroism responsive to anion binding

Cited by 22 publications

References 32 publications

Ion and Molecular Recognition Using Aryl–Ethynyl Scaffolding

Ion and Molecular Recognition Using Aryl–Ethynyl Scaffolding

Anion receptors with 1,3,5‐triazacyclohexane and 1,4,7,10‐tetraazacyclododecane scaffolds

Helical Folding Competing with Unfolded Aggregation in Phenylene Ethynylene Foldamers

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