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 A Zubieta, Jens Beckmann, Hajo Haase, Gündoǧ Yücesan

Research output: Contribution to journalArticle

2 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)2152-2158
Number of pages7
JournalCrystEngComm
Volume20
Issue number15
DOIs
StatePublished - Jan 1 2018

Fingerprint

Organophosphonates
Phospholipids
Metals
Crystalline materials
solid state
acids
Acids
Naphthalene
cells
naphthalene
toxicity
metals
Molecular structure
Toxicity
Zinc
Photoluminescence
molecular structure
zinc
Fluorescence
Single crystals

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

Mimicking cellular phospholipid bilayer packing creates predictable crystalline molecular metal-organophosphonate macrocycles and cages. / Bulut, Aysun; Maares, Maria; Atak, Kaan; Zorlu, Yunus; Çoşut, Bünyemin; Zubieta, Jon A; Beckmann, Jens; Haase, Hajo; Yücesan, Gündoǧ.

In: CrystEngComm, Vol. 20, No. 15, 01.01.2018, p. 2152-2158.

Research output: Contribution to journalArticle

Bulut, A, Maares, M, Atak, K, Zorlu, Y, Çoşut, B, Zubieta, JA, Beckmann, J, Haase, H & Yücesan, G 2018, 'Mimicking cellular phospholipid bilayer packing creates predictable crystalline molecular metal-organophosphonate macrocycles and cages', CrystEngComm, vol. 20, no. 15, pp. 2152-2158. https://doi.org/10.1039/c8ce00072g
Bulut, Aysun ; Maares, Maria ; Atak, Kaan ; Zorlu, Yunus ; Çoşut, Bünyemin ; Zubieta, Jon A ; Beckmann, Jens ; Haase, Hajo ; Yücesan, Gündoǧ. / Mimicking cellular phospholipid bilayer packing creates predictable crystalline molecular metal-organophosphonate macrocycles and cages. In: CrystEngComm. 2018 ; Vol. 20, No. 15. pp. 2152-2158.
@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 {\cC}oşut and Zubieta, {Jon A} and Jens Beckmann and Hajo Haase and G{\"u}ndoǧ Y{\"u}cesan",
year = "2018",
month = "1",
day = "1",
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 A

AU - Beckmann, Jens

AU - Haase, Hajo

AU - Yücesan, Gündoǧ

PY - 2018/1/1

Y1 - 2018/1/1

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

VL - 20

SP - 2152

EP - 2158

JO - CrystEngComm

JF - CrystEngComm

SN - 1466-8033

IS - 15

ER -