Hexaphenolic Rigid Cages Prepared by Self-Organization of C 3v Tridentates

Hajime Abe; Daisuke Hashikawa; Takaya Minami; Kohei Ohtani; Kentaro Masuda; Shinya Matsumoto; Masahiko Inouye

doi:10.1021/acs.joc.7b03111

Hexaphenolic Rigid Cages Prepared by Self-Organization of C _3v Tridentates

Hajime Abe^*, Daisuke Hashikawa, Takaya Minami, Kohei Ohtani, Kentaro Masuda, Shinya Matsumoto, Masahiko Inouye

^*Corresponding author for this work

Member of the Board

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

4 Scopus citations

Abstract

Coordination cages were composed by self-organization of rigid C_3v-symmetric heptaarene tridentates and Pd(II) precursors. The heptaarene framework involves one mesitylene, three phenol, and three pyridine moieties, which were connected by Suzuki coupling reactions. The treatment of the tridentates with Pd(dppp)(OTf)₂ or Pd(en)(NO₃)₂ in a 2:3 molar ratio furnished coordination cages, which was ascertained by crystallography, ¹H NMR and DOSY measurements, and ESI-TOFMS and UV-vis spectra. The cages have six phenolic hydroxy groups inside and were expected to incorporate hydrogen-bonding guest molecules such as saccharides. CD and DOSY measurements showed that octyl hexoside guests could be incorporated into the cage.

Original language	English
Pages (from-to)	3132-3141
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	83
Issue number	6
DOIs	https://doi.org/10.1021/acs.joc.7b03111
State	Published - 2018/03/16

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/acs.joc.7b03111

Cite this

@article{9f56d8ea2f8642d08fc358811f42e872,

title = "Hexaphenolic Rigid Cages Prepared by Self-Organization of C 3v Tridentates",

abstract = "Coordination cages were composed by self-organization of rigid C3v-symmetric heptaarene tridentates and Pd(II) precursors. The heptaarene framework involves one mesitylene, three phenol, and three pyridine moieties, which were connected by Suzuki coupling reactions. The treatment of the tridentates with Pd(dppp)(OTf)2 or Pd(en)(NO3)2 in a 2:3 molar ratio furnished coordination cages, which was ascertained by crystallography, 1H NMR and DOSY measurements, and ESI-TOFMS and UV-vis spectra. The cages have six phenolic hydroxy groups inside and were expected to incorporate hydrogen-bonding guest molecules such as saccharides. CD and DOSY measurements showed that octyl hexoside guests could be incorporated into the cage.",

author = "Hajime Abe and Daisuke Hashikawa and Takaya Minami and Kohei Ohtani and Kentaro Masuda and Shinya Matsumoto and Masahiko Inouye",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = mar,

day = "16",

doi = "10.1021/acs.joc.7b03111",

language = "英語",

volume = "83",

pages = "3132--3141",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Hexaphenolic Rigid Cages Prepared by Self-Organization of C 3v Tridentates

AU - Abe, Hajime

AU - Hashikawa, Daisuke

AU - Minami, Takaya

AU - Ohtani, Kohei

AU - Masuda, Kentaro

AU - Matsumoto, Shinya

AU - Inouye, Masahiko

PY - 2018/3/16

Y1 - 2018/3/16

N2 - Coordination cages were composed by self-organization of rigid C3v-symmetric heptaarene tridentates and Pd(II) precursors. The heptaarene framework involves one mesitylene, three phenol, and three pyridine moieties, which were connected by Suzuki coupling reactions. The treatment of the tridentates with Pd(dppp)(OTf)2 or Pd(en)(NO3)2 in a 2:3 molar ratio furnished coordination cages, which was ascertained by crystallography, 1H NMR and DOSY measurements, and ESI-TOFMS and UV-vis spectra. The cages have six phenolic hydroxy groups inside and were expected to incorporate hydrogen-bonding guest molecules such as saccharides. CD and DOSY measurements showed that octyl hexoside guests could be incorporated into the cage.

AB - Coordination cages were composed by self-organization of rigid C3v-symmetric heptaarene tridentates and Pd(II) precursors. The heptaarene framework involves one mesitylene, three phenol, and three pyridine moieties, which were connected by Suzuki coupling reactions. The treatment of the tridentates with Pd(dppp)(OTf)2 or Pd(en)(NO3)2 in a 2:3 molar ratio furnished coordination cages, which was ascertained by crystallography, 1H NMR and DOSY measurements, and ESI-TOFMS and UV-vis spectra. The cages have six phenolic hydroxy groups inside and were expected to incorporate hydrogen-bonding guest molecules such as saccharides. CD and DOSY measurements showed that octyl hexoside guests could be incorporated into the cage.

UR - http://www.scopus.com/inward/record.url?scp=85044129676&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.7b03111

DO - 10.1021/acs.joc.7b03111

M3 - 学術論文

C2 - 29473751

AN - SCOPUS:85044129676

SN - 0022-3263

VL - 83

SP - 3132

EP - 3141

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6