Helquat-induced chiroselective aggregation of Au NPs

Dora Balogh; Zhanxia Zhang; Alessandro Cecconello; Jan Vavra; Lukas Severa; Filip Teply; Itamar Willner

doi:10.1021/nl303179s

Helquat-induced chiroselective aggregation of Au NPs

Dora Balogh, Zhanxia Zhang, Alessandro Cecconello, Jan Vavra, Lukas Severa, Filip Teply^*, Itamar Willner

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

Abstract

Au nanoparticles (NPs) are functionalized with chiral (R) or (S) binaphthol phenylboronic acid ligands, (1a) or (1b). The (R)- or (S)-binaphthol phenylboronic acid ligands form donor-acceptor complexes with the chiral dicationic helicene, helquat (P)-HQ²⁺ or (M)-HQ²⁺, (2a) or (2b). The association constants between (1a)/(2a) and (1a)/(2b) correspond to (7.0 ± 0.5) × 10⁵ M^-1 and (2.5 ± 0.3) × 10⁵ M^-1, respectively, whereas the association constants between (1b)/(2b) and (1b)/(2a) correspond to (4.0 ± 0.5) × 10⁵ M^-1 and (1.8 ± 0.3) × 10 ⁵ M^-1, respectively. Chiroselective aggregation of chiral binaphthol phenylboronic acid-capped Au NPs triggered by the chiral helquats, is demonstrated.

Original language	English
Pages (from-to)	5835-5839
Number of pages	5
Journal	Nano Letters
Volume	12
Issue number	11
DOIs	https://doi.org/10.1021/nl303179s
State	Published - 14 Nov 2012

Keywords

Nanoparticles
aggregation
binaphthol phenylboronic acid
chirality
donor-acceptor interactions
helquat

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10.1021/nl303179s

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title = "Helquat-induced chiroselective aggregation of Au NPs",

abstract = "Au nanoparticles (NPs) are functionalized with chiral (R) or (S) binaphthol phenylboronic acid ligands, (1a) or (1b). The (R)- or (S)-binaphthol phenylboronic acid ligands form donor-acceptor complexes with the chiral dicationic helicene, helquat (P)-HQ2+ or (M)-HQ2+, (2a) or (2b). The association constants between (1a)/(2a) and (1a)/(2b) correspond to (7.0 ± 0.5) × 105 M-1 and (2.5 ± 0.3) × 105 M-1, respectively, whereas the association constants between (1b)/(2b) and (1b)/(2a) correspond to (4.0 ± 0.5) × 105 M-1 and (1.8 ± 0.3) × 10 5 M-1, respectively. Chiroselective aggregation of chiral binaphthol phenylboronic acid-capped Au NPs triggered by the chiral helquats, is demonstrated.",

keywords = "Nanoparticles, aggregation, binaphthol phenylboronic acid, chirality, donor-acceptor interactions, helquat",

author = "Dora Balogh and Zhanxia Zhang and Alessandro Cecconello and Jan Vavra and Lukas Severa and Filip Teply and Itamar Willner",

year = "2012",

month = nov,

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doi = "10.1021/nl303179s",

language = "אנגלית",

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T1 - Helquat-induced chiroselective aggregation of Au NPs

AU - Balogh, Dora

AU - Zhang, Zhanxia

AU - Cecconello, Alessandro

AU - Vavra, Jan

AU - Severa, Lukas

AU - Teply, Filip

AU - Willner, Itamar

PY - 2012/11/14

Y1 - 2012/11/14

N2 - Au nanoparticles (NPs) are functionalized with chiral (R) or (S) binaphthol phenylboronic acid ligands, (1a) or (1b). The (R)- or (S)-binaphthol phenylboronic acid ligands form donor-acceptor complexes with the chiral dicationic helicene, helquat (P)-HQ2+ or (M)-HQ2+, (2a) or (2b). The association constants between (1a)/(2a) and (1a)/(2b) correspond to (7.0 ± 0.5) × 105 M-1 and (2.5 ± 0.3) × 105 M-1, respectively, whereas the association constants between (1b)/(2b) and (1b)/(2a) correspond to (4.0 ± 0.5) × 105 M-1 and (1.8 ± 0.3) × 10 5 M-1, respectively. Chiroselective aggregation of chiral binaphthol phenylboronic acid-capped Au NPs triggered by the chiral helquats, is demonstrated.

AB - Au nanoparticles (NPs) are functionalized with chiral (R) or (S) binaphthol phenylboronic acid ligands, (1a) or (1b). The (R)- or (S)-binaphthol phenylboronic acid ligands form donor-acceptor complexes with the chiral dicationic helicene, helquat (P)-HQ2+ or (M)-HQ2+, (2a) or (2b). The association constants between (1a)/(2a) and (1a)/(2b) correspond to (7.0 ± 0.5) × 105 M-1 and (2.5 ± 0.3) × 105 M-1, respectively, whereas the association constants between (1b)/(2b) and (1b)/(2a) correspond to (4.0 ± 0.5) × 105 M-1 and (1.8 ± 0.3) × 10 5 M-1, respectively. Chiroselective aggregation of chiral binaphthol phenylboronic acid-capped Au NPs triggered by the chiral helquats, is demonstrated.

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KW - aggregation

KW - binaphthol phenylboronic acid

KW - chirality

KW - donor-acceptor interactions

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Helquat-induced chiroselective aggregation of Au NPs

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