Mimicking cellular phospholipid bilayer packing creates predictable crystalline molecular metal-organophosphonate macrocycles and cages

Aysun Bulut; Maria Maares; Kaan Atak; Yunus Zorlu; Bünyemin Çoşut; Jon Zubieta; Jens Beckmann; Hajo Haase; Gündoǧ Yücesan

doi:10.1039/c8ce00072g

Mimicking cellular phospholipid bilayer packing creates predictable crystalline molecular metal-organophosphonate macrocycles and cages

Aysun Bulut, Maria Maares, Kaan Atak, Yunus Zorlu, Bünyemin Çoşut, Jon Zubieta, Jens Beckmann, Hajo Haase, Gündoǧ Yücesan

Department of Chemistry

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

6 Scopus citations

Abstract

We report a novel mechanism to create a predictable molecular metal-organophosphonate cage [Zn₂(2,2′-bpy)₂(H₂ODP)₂(H₄ODP)]·2H₂O (1·2H₂O) (H₄ODP = 1,8-octanediphosphonic acid) and a macrocycle [Cu₂(2,2′-bpy)₂(H₂-1,4-NDPA)₂(H₂O)₂]·H₂O (2) (H₄-1,4-NDPA = 1,4-naphthalene diphosphonic acid). The structures were solved using single crystal X-ray diffraction. The photoluminescence properties of 1·2H₂O, investigated both in solution and in the solid-state at room temperature, indicated that the tighter zinc binding in the solid state leads to the augmentation of fluorescence. The ORCA molecular structure optimization calculations for 1·2H₂O suggest a slight opening of the cage structure in non-polar solvents while in polar solvents the cage is tightened. Toxicity analysis with Caco-2 cells indicates that the molecule is readily tolerated by intestinal cells.

Original language	English (US)
Pages (from-to)	2152-2158
Number of pages	7
Journal	CrystEngComm
Volume	20
Issue number	15
DOIs	https://doi.org/10.1039/c8ce00072g
State	Published - 2018

ASJC Scopus subject areas

General Chemistry
General Materials Science
Condensed Matter Physics

Access to Document

10.1039/c8ce00072g

Cite this

@article{ce589486cf2c4b7896e4d88cbf198b51,

title = "Mimicking cellular phospholipid bilayer packing creates predictable crystalline molecular metal-organophosphonate macrocycles and cages",

abstract = "We report a novel mechanism to create a predictable molecular metal-organophosphonate cage [Zn2(2,2′-bpy)2(H2ODP)2(H4ODP)]·2H2O (1·2H2O) (H4ODP = 1,8-octanediphosphonic acid) and a macrocycle [Cu2(2,2′-bpy)2(H2-1,4-NDPA)2(H2O)2]·H2O (2) (H4-1,4-NDPA = 1,4-naphthalene diphosphonic acid). The structures were solved using single crystal X-ray diffraction. The photoluminescence properties of 1·2H2O, investigated both in solution and in the solid-state at room temperature, indicated that the tighter zinc binding in the solid state leads to the augmentation of fluorescence. The ORCA molecular structure optimization calculations for 1·2H2O suggest a slight opening of the cage structure in non-polar solvents while in polar solvents the cage is tightened. Toxicity analysis with Caco-2 cells indicates that the molecule is readily tolerated by intestinal cells.",

author = "Aysun Bulut and Maria Maares and Kaan Atak and Yunus Zorlu and B{\"u}nyemin {\c C}o{\c s}ut and Jon Zubieta and Jens Beckmann and Hajo Haase and G{\"u}ndoǧ Y{\"u}cesan",

note = "Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c8ce00072g",

language = "English (US)",

volume = "20",

pages = "2152--2158",

journal = "CrystEngComm",

issn = "1466-8033",

publisher = "Royal Society of Chemistry",

number = "15",

}

TY - JOUR

T1 - Mimicking cellular phospholipid bilayer packing creates predictable crystalline molecular metal-organophosphonate macrocycles and cages

AU - Bulut, Aysun

AU - Maares, Maria

AU - Atak, Kaan

AU - Zorlu, Yunus

AU - Çoşut, Bünyemin

AU - Zubieta, Jon

AU - Beckmann, Jens

AU - Haase, Hajo

AU - Yücesan, Gündoǧ

PY - 2018

Y1 - 2018

N2 - We report a novel mechanism to create a predictable molecular metal-organophosphonate cage [Zn2(2,2′-bpy)2(H2ODP)2(H4ODP)]·2H2O (1·2H2O) (H4ODP = 1,8-octanediphosphonic acid) and a macrocycle [Cu2(2,2′-bpy)2(H2-1,4-NDPA)2(H2O)2]·H2O (2) (H4-1,4-NDPA = 1,4-naphthalene diphosphonic acid). The structures were solved using single crystal X-ray diffraction. The photoluminescence properties of 1·2H2O, investigated both in solution and in the solid-state at room temperature, indicated that the tighter zinc binding in the solid state leads to the augmentation of fluorescence. The ORCA molecular structure optimization calculations for 1·2H2O suggest a slight opening of the cage structure in non-polar solvents while in polar solvents the cage is tightened. Toxicity analysis with Caco-2 cells indicates that the molecule is readily tolerated by intestinal cells.

AB - We report a novel mechanism to create a predictable molecular metal-organophosphonate cage [Zn2(2,2′-bpy)2(H2ODP)2(H4ODP)]·2H2O (1·2H2O) (H4ODP = 1,8-octanediphosphonic acid) and a macrocycle [Cu2(2,2′-bpy)2(H2-1,4-NDPA)2(H2O)2]·H2O (2) (H4-1,4-NDPA = 1,4-naphthalene diphosphonic acid). The structures were solved using single crystal X-ray diffraction. The photoluminescence properties of 1·2H2O, investigated both in solution and in the solid-state at room temperature, indicated that the tighter zinc binding in the solid state leads to the augmentation of fluorescence. The ORCA molecular structure optimization calculations for 1·2H2O suggest a slight opening of the cage structure in non-polar solvents while in polar solvents the cage is tightened. Toxicity analysis with Caco-2 cells indicates that the molecule is readily tolerated by intestinal cells.

UR - http://www.scopus.com/inward/record.url?scp=85045578929&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85045578929&partnerID=8YFLogxK

U2 - 10.1039/c8ce00072g

DO - 10.1039/c8ce00072g

M3 - Article

AN - SCOPUS:85045578929

SN - 1466-8033

VL - 20

SP - 2152

EP - 2158

JO - CrystEngComm

JF - CrystEngComm

IS - 15

ER -

Mimicking cellular phospholipid bilayer packing creates predictable crystalline molecular metal-organophosphonate macrocycles and cages

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this