Alkoxy Substituted Brominated closo-Dodecaborates with Functionalized Aliphatic Spacers

Satoshi Yamamoto; Hibiki Nakamura; Yumiko K. Kawamura; Taro Kitazawa; Mutsumi Kimura; Yu Kitazawa

doi:10.3390/chemistry6060099

Alkoxy Substituted Brominated closo-Dodecaborates with Functionalized Aliphatic Spacers

Satoshi Yamamoto, Hibiki Nakamura, Yumiko K. Kawamura, Taro Kitazawa^*, Mutsumi Kimura, Yu Kitazawa^*

^*Corresponding author af dette arbejde

Institut for Molekylærbiologi og Genetik - Neurobiologi

Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avis › Tidsskriftartikel › Forskning › peer review

Abstract

The utilization of dodecaborate boron clusters, [B₁₂X₁₂]²⁻ (X = Cl, Br, or I), as membrane carriers has been demonstrated recently, and their activity is known to be due to their superchaotropic nature. In this work, the mono-alkylation of [B₁₂Br₁₁OH]²⁻ to functionalize it with an aliphatic spacer was developed with a view to expanding the known chemical space of membrane carriers based on [B₁₂Br₁₂]²⁻. A new and improved facile route for the preparation of [B₁₂Br₁₁OH]²⁻, which is an important precursor to other [B₁₂Br₁₁OR]²⁻ species, is reported. Various alkoxylated [B₁₂Br₁₁O(CH₂)₅Z]²⁻ (Z = OH, N(CO)₂C₆H₄, CN and N₃) derivatives were prepared via a divergent synthesis based on [B₁₂Br₁₁O(CH₂)₅Br]²⁻. One of the newly synthesized compounds was utilized as a membrane carrier, and its impact on cell viability was examined.

Originalsprog	Engelsk
Tidsskrift	Chemistry (Switzerland)
Vol/bind	6
Nummer	6
Sider (fra-til)	1635-1644
Antal sider	10
ISSN	2624-8549
DOI	https://doi.org/10.3390/chemistry6060099
Status	Udgivet - dec. 2024

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10.3390/chemistry6060099

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title = "Alkoxy Substituted Brominated closo-Dodecaborates with Functionalized Aliphatic Spacers",

abstract = "The utilization of dodecaborate boron clusters, [B12X12]2− (X = Cl, Br, or I), as membrane carriers has been demonstrated recently, and their activity is known to be due to their superchaotropic nature. In this work, the mono-alkylation of [B12Br11OH]2− to functionalize it with an aliphatic spacer was developed with a view to expanding the known chemical space of membrane carriers based on [B12Br12]2−. A new and improved facile route for the preparation of [B12Br11OH]2−, which is an important precursor to other [B12Br11OR]2− species, is reported. Various alkoxylated [B12Br11O(CH2)5Z]2− (Z = OH, N(CO)2C6H4, CN and N3) derivatives were prepared via a divergent synthesis based on [B12Br11O(CH2)5Br]2−. One of the newly synthesized compounds was utilized as a membrane carrier, and its impact on cell viability was examined.",

keywords = "boron cluster, chaotropic, membrane transport",

author = "Satoshi Yamamoto and Hibiki Nakamura and Kawamura, {Yumiko K.} and Taro Kitazawa and Mutsumi Kimura and Yu Kitazawa",

note = "Publisher Copyright: {\textcopyright} 2024 by the authors.",

year = "2024",

month = dec,

doi = "10.3390/chemistry6060099",

language = "English",

volume = "6",

pages = "1635--1644",

journal = "Chemistry (Switzerland)",

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T1 - Alkoxy Substituted Brominated closo-Dodecaborates with Functionalized Aliphatic Spacers

AU - Yamamoto, Satoshi

AU - Nakamura, Hibiki

AU - Kawamura, Yumiko K.

AU - Kitazawa, Taro

AU - Kimura, Mutsumi

AU - Kitazawa, Yu

PY - 2024/12

Y1 - 2024/12

N2 - The utilization of dodecaborate boron clusters, [B12X12]2− (X = Cl, Br, or I), as membrane carriers has been demonstrated recently, and their activity is known to be due to their superchaotropic nature. In this work, the mono-alkylation of [B12Br11OH]2− to functionalize it with an aliphatic spacer was developed with a view to expanding the known chemical space of membrane carriers based on [B12Br12]2−. A new and improved facile route for the preparation of [B12Br11OH]2−, which is an important precursor to other [B12Br11OR]2− species, is reported. Various alkoxylated [B12Br11O(CH2)5Z]2− (Z = OH, N(CO)2C6H4, CN and N3) derivatives were prepared via a divergent synthesis based on [B12Br11O(CH2)5Br]2−. One of the newly synthesized compounds was utilized as a membrane carrier, and its impact on cell viability was examined.

AB - The utilization of dodecaborate boron clusters, [B12X12]2− (X = Cl, Br, or I), as membrane carriers has been demonstrated recently, and their activity is known to be due to their superchaotropic nature. In this work, the mono-alkylation of [B12Br11OH]2− to functionalize it with an aliphatic spacer was developed with a view to expanding the known chemical space of membrane carriers based on [B12Br12]2−. A new and improved facile route for the preparation of [B12Br11OH]2−, which is an important precursor to other [B12Br11OR]2− species, is reported. Various alkoxylated [B12Br11O(CH2)5Z]2− (Z = OH, N(CO)2C6H4, CN and N3) derivatives were prepared via a divergent synthesis based on [B12Br11O(CH2)5Br]2−. One of the newly synthesized compounds was utilized as a membrane carrier, and its impact on cell viability was examined.

KW - boron cluster

KW - chaotropic

KW - membrane transport

UR - http://www.scopus.com/inward/record.url?scp=85213437999&partnerID=8YFLogxK

U2 - 10.3390/chemistry6060099

DO - 10.3390/chemistry6060099

M3 - Journal article

AN - SCOPUS:85213437999

SN - 2624-8549

VL - 6

SP - 1635

EP - 1644

JO - Chemistry (Switzerland)

JF - Chemistry (Switzerland)

IS - 6

ER -

Alkoxy Substituted Brominated closo-Dodecaborates with Functionalized Aliphatic Spacers

Abstract

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