Unraveling the molecular recognition of "three methylene spacer" bis(benzimidazolium) moiety by dibenzo-24-crown-8: Pseudorotaxanes under study

Chhanda Mukhopadhyay, Sabari Ghosh, Ann Marie Schmiedekamp

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

"Three methylene spacer" bis(benzimidazolium) derivatives act as a new template for threading dibenzo-24-crown-8 into [2]pseudorotaxanes. In this Article we sought to unveil the difference in the extent of threading of various "three methylene spacer" bis-benzimidazolium moieties based on differences in aromatic methyl substituent positions and anions through the macrocycle dibenzo-24-crown-8. The temperature of the systems were also varied (low temperatures of 240 K and 253 K), when such interwinding of the thread and crown were not detected at room temperature of 308 K. The presence of such threaded complexes was determined based on 1H-NMR initially and finally corroborated by high resolution mass spectrometry and DFT calculations. 2D-NMR experiments ( 1H- 1H-NOESY) proved to be a very important tool in elucidating the interaction present between the components of the pseudorotaxanes. The dethreading/rethreading process was studied. DFT optimized structures suggest lower energy H-bonding orientations and compare the effect of methyl substituents on the axle.

Original languageEnglish (US)
Pages (from-to)1434-1439
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number7
DOIs
StatePublished - Feb 21 2012

Fingerprint

Rotaxanes
Molecular recognition
methylene
spacers
Discrete Fourier transforms
nuclear magnetic resonance
Temperature
threads
Nuclear magnetic resonance
mass spectroscopy
templates
Axles
anions
Crowns
Anions
Mass spectrometry
high resolution
Mass Spectrometry
room temperature
Derivatives

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

@article{422e47d675284ca59f167bf208eeeed8,
title = "Unraveling the molecular recognition of {"}three methylene spacer{"} bis(benzimidazolium) moiety by dibenzo-24-crown-8: Pseudorotaxanes under study",
abstract = "{"}Three methylene spacer{"} bis(benzimidazolium) derivatives act as a new template for threading dibenzo-24-crown-8 into [2]pseudorotaxanes. In this Article we sought to unveil the difference in the extent of threading of various {"}three methylene spacer{"} bis-benzimidazolium moieties based on differences in aromatic methyl substituent positions and anions through the macrocycle dibenzo-24-crown-8. The temperature of the systems were also varied (low temperatures of 240 K and 253 K), when such interwinding of the thread and crown were not detected at room temperature of 308 K. The presence of such threaded complexes was determined based on 1H-NMR initially and finally corroborated by high resolution mass spectrometry and DFT calculations. 2D-NMR experiments ( 1H- 1H-NOESY) proved to be a very important tool in elucidating the interaction present between the components of the pseudorotaxanes. The dethreading/rethreading process was studied. DFT optimized structures suggest lower energy H-bonding orientations and compare the effect of methyl substituents on the axle.",
author = "Chhanda Mukhopadhyay and Sabari Ghosh and Schmiedekamp, {Ann Marie}",
year = "2012",
month = "2",
day = "21",
doi = "10.1039/c1ob06311a",
language = "English (US)",
volume = "10",
pages = "1434--1439",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "7",

}

Unraveling the molecular recognition of "three methylene spacer" bis(benzimidazolium) moiety by dibenzo-24-crown-8 : Pseudorotaxanes under study. / Mukhopadhyay, Chhanda; Ghosh, Sabari; Schmiedekamp, Ann Marie.

In: Organic and Biomolecular Chemistry, Vol. 10, No. 7, 21.02.2012, p. 1434-1439.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Unraveling the molecular recognition of "three methylene spacer" bis(benzimidazolium) moiety by dibenzo-24-crown-8

T2 - Pseudorotaxanes under study

AU - Mukhopadhyay, Chhanda

AU - Ghosh, Sabari

AU - Schmiedekamp, Ann Marie

PY - 2012/2/21

Y1 - 2012/2/21

N2 - "Three methylene spacer" bis(benzimidazolium) derivatives act as a new template for threading dibenzo-24-crown-8 into [2]pseudorotaxanes. In this Article we sought to unveil the difference in the extent of threading of various "three methylene spacer" bis-benzimidazolium moieties based on differences in aromatic methyl substituent positions and anions through the macrocycle dibenzo-24-crown-8. The temperature of the systems were also varied (low temperatures of 240 K and 253 K), when such interwinding of the thread and crown were not detected at room temperature of 308 K. The presence of such threaded complexes was determined based on 1H-NMR initially and finally corroborated by high resolution mass spectrometry and DFT calculations. 2D-NMR experiments ( 1H- 1H-NOESY) proved to be a very important tool in elucidating the interaction present between the components of the pseudorotaxanes. The dethreading/rethreading process was studied. DFT optimized structures suggest lower energy H-bonding orientations and compare the effect of methyl substituents on the axle.

AB - "Three methylene spacer" bis(benzimidazolium) derivatives act as a new template for threading dibenzo-24-crown-8 into [2]pseudorotaxanes. In this Article we sought to unveil the difference in the extent of threading of various "three methylene spacer" bis-benzimidazolium moieties based on differences in aromatic methyl substituent positions and anions through the macrocycle dibenzo-24-crown-8. The temperature of the systems were also varied (low temperatures of 240 K and 253 K), when such interwinding of the thread and crown were not detected at room temperature of 308 K. The presence of such threaded complexes was determined based on 1H-NMR initially and finally corroborated by high resolution mass spectrometry and DFT calculations. 2D-NMR experiments ( 1H- 1H-NOESY) proved to be a very important tool in elucidating the interaction present between the components of the pseudorotaxanes. The dethreading/rethreading process was studied. DFT optimized structures suggest lower energy H-bonding orientations and compare the effect of methyl substituents on the axle.

UR - http://www.scopus.com/inward/record.url?scp=84856747593&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84856747593&partnerID=8YFLogxK

U2 - 10.1039/c1ob06311a

DO - 10.1039/c1ob06311a

M3 - Article

C2 - 22212620

AN - SCOPUS:84856747593

VL - 10

SP - 1434

EP - 1439

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 7

ER -