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Title: Formation of a Fluorous/Organic Biphasic Supramolecular Octopus Assembly for Enhanced Porphyrin Phosphorescence in Air

Abstract

The trinuclear triangle-shaped system [tris{3,5-bis(heptafluoropropyl)-1,2,4-triazolatosilver(I)}] (1) and the multi-armed square-shaped metalloporphyrin PtOEP or the free porphyrin base H2OEP serve as excellent octopus hosts (OEP=2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphine). Coupling of the fluorous/organic molecular octopi 1 and H2OEP or PtOEP by strong quadrupole-quadrupole and metal- interactions affords the supramolecular assemblies [1PtOEP] or [1H(2)OEP] (2a), which feature nanoscopic cavities surrounding the upper triangular and lower square cores. The fluorous/organic biphasic configuration of [1PtOEP] leads to an increase in the phosphorescence of PtOEP under ambient conditions. Guest molecules can be included in the biphasic double-octopus assembly in three different site-selective modes.

Authors:
 [1];  [1];  [1];  [1];  [1];  [2];  [1]
+ Show Author Affiliations
  1. Univ. of North Texas, Denton, TX (United States)
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Publication Date:
Research Org.:
Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1335317
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
Angewandte Chemie International Edition (Online)
Additional Journal Information:
Journal Name: Angewandte Chemie International Edition (Online); Journal Volume: 54; Journal Issue: 16; Journal ID: ISSN 1521-3773
Publisher:
Gesselschaft Deutscher Chemiker
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; fluorine; heterocycles; luminescent materials; porphyrins; supramolecular chemistry; METAL-ORGANIC FRAMEWORKS; LIGHT-EMITTING DEVICES; COORDINATION NETWORKS; GAS-ADSORPTION; COMPLEXES; MOLECULES; CHEMISTRY; DIFFUSION; CHAIN

Citation Formats

Yang, Chi, Arvapally, Ravi K., Tekarli, Sammer M., Salazar, Gustavo A., Elbjeirami, Oussama, Wang, Xiaoping, and Omary, Mohammad A. Formation of a Fluorous/Organic Biphasic Supramolecular Octopus Assembly for Enhanced Porphyrin Phosphorescence in Air. United States: N. p., 2015. Web. doi:10.1002/anie.201411462.
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Yang, Chi, Arvapally, Ravi K., Tekarli, Sammer M., Salazar, Gustavo A., Elbjeirami, Oussama, Wang, Xiaoping, & Omary, Mohammad A. Formation of a Fluorous/Organic Biphasic Supramolecular Octopus Assembly for Enhanced Porphyrin Phosphorescence in Air. United States. https://doi.org/10.1002/anie.201411462
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Yang, Chi, Arvapally, Ravi K., Tekarli, Sammer M., Salazar, Gustavo A., Elbjeirami, Oussama, Wang, Xiaoping, and Omary, Mohammad A. Tue . "Formation of a Fluorous/Organic Biphasic Supramolecular Octopus Assembly for Enhanced Porphyrin Phosphorescence in Air". United States. https://doi.org/10.1002/anie.201411462. https://www.osti.gov/servlets/purl/1335317.
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@article{osti_1335317,
title = {Formation of a Fluorous/Organic Biphasic Supramolecular Octopus Assembly for Enhanced Porphyrin Phosphorescence in Air},
author = {Yang, Chi and Arvapally, Ravi K. and Tekarli, Sammer M. and Salazar, Gustavo A. and Elbjeirami, Oussama and Wang, Xiaoping and Omary, Mohammad A.},
abstractNote = {The trinuclear triangle-shaped system [tris{3,5-bis(heptafluoropropyl)-1,2,4-triazolatosilver(I)}] (1) and the multi-armed square-shaped metalloporphyrin PtOEP or the free porphyrin base H2OEP serve as excellent octopus hosts (OEP=2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphine). Coupling of the fluorous/organic molecular octopi 1 and H2OEP or PtOEP by strong quadrupole-quadrupole and metal- interactions affords the supramolecular assemblies [1PtOEP] or [1H(2)OEP] (2a), which feature nanoscopic cavities surrounding the upper triangular and lower square cores. The fluorous/organic biphasic configuration of [1PtOEP] leads to an increase in the phosphorescence of PtOEP under ambient conditions. Guest molecules can be included in the biphasic double-octopus assembly in three different site-selective modes.},
doi = {10.1002/anie.201411462},
journal = {Angewandte Chemie International Edition (Online)},
number = 16,
volume = 54,
place = {United States},
year = {Tue Mar 03 00:00:00 EST 2015},
month = {Tue Mar 03 00:00:00 EST 2015}
}
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Journal Article:
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https://doi.org/10.1002/anie.201411462
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Cited by: 7 works
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Figures / Tables:

Scheme 1 Scheme 1: a, b) Chemical structure (a) and MEPs (b) of H2OEP, PtOEP, and 1 mapped on the electron density surfaces. c) Formation of biphasic double-octopus assembly 2 by quadrupole–quadrupole interactions. Three different guest-inclusion modes are possible: i) head-on inclusion of a linear guest within the fluorous cavity; ii) inclusion of an aromatic guest within the nest consisting of a semi-fluorous phase and a semi-organic phase; iii) inclusion of an aromatic p-dimer within the fluorous cage while an aromatic monomer is included within the organic cage.more » $\blacksquare$$\blacksquare$Please clarify the units. What does “a.u.” stand for? Does “-4.63E-2” mean “-4.63 x 10"?$\blacksquare$$\blacksquare$« less
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Works referenced in this record:

Expected and Unconventional Ag+ Binding Modes in Heteronuclear Pt,Ag Coordination Polymers Derived from trans-[Pt(methylamine)2(pyrazole)2]2+
journal, January 2012

  • Brandi-Blanco, Pilar; Sanz Miguel, Pablo J.; Lippert, Bernhard
  • European Journal of Inorganic Chemistry, Vol. 2012, Issue 7
  • DOI: 10.1002/ejic.201101197

Bioinspired Detection of Light Using a Porphyrin-Sensitized Single-Wall Nanotube Field Effect Transistor
journal, September 2006

  • Hecht, David S.; Ramirez, Robert J. A.; Briman, Mikhail
  • Nano Letters, Vol. 6, Issue 9
  • DOI: 10.1021/nl061231s

Stacked Platinum Complexes of the Magnus’ Salt Type Inside a Coordination Cage
journal, January 2012

  • Clever, Guido H.; Kawamura, Wataru; Tashiro, Shohei
  • Angewandte Chemie International Edition, Vol. 51, Issue 11
  • DOI: 10.1002/anie.201108197

Remarkably Simple Fabrication of Superhydrophobic Surfaces Using Electroless Galvanic Deposition
journal, February 2007

  • Larmour, Iain A.; Bell, Steven E. J.; Saunders, Graham C.
  • Angewandte Chemie International Edition, Vol. 46, Issue 10
  • DOI: 10.1002/anie.200604596

Trinuclear Gold(I) Triazolates:  A New Class of Wide-Band Phosphors and Sensors
journal, August 2006

  • Yang, Chi; Messerschmidt, Marc; Coppens, Philip
  • Inorganic Chemistry, Vol. 45, Issue 17
  • DOI: 10.1021/ic060943i

Functionalized Coordination Space in Metal-Organic Frameworks
journal, October 2008

  • Fischer, Roland A.; Wöll, Christof
  • Angewandte Chemie International Edition, Vol. 47, Issue 43
  • DOI: 10.1002/anie.200801612

Novel optical oxygen sensing material: platinum porphyrin-fluoropolymer film
journal, January 2000

Syntheses of macrocyclic enzyme models. 7. Octopus cyclophanes having L-aspartate residues as novel water-soluble hosts; aggregation behavior and induced-fit molecular recognition
journal, October 1990

  • Murakami, Yukito; Kikuchi, Junichi; Ohno, Teruhisa
  • Journal of the American Chemical Society, Vol. 112, Issue 21
  • DOI: 10.1021/ja00177a031

Fluorous Metal−Organic Frameworks for High-Density Gas Adsorption
journal, December 2007

  • Yang, Chi; Wang, Xiaoping; Omary, Mohammad A.
  • Journal of the American Chemical Society, Vol. 129, Issue 50
  • DOI: 10.1021/ja0775265

Engineering discrete stacks of aromatic molecules
journal, January 2009

  • Klosterman, Jeremy K.; Yamauchi, Yoshihiro; Fujita, Makoto
  • Chemical Society Reviews, Vol. 38, Issue 6
  • DOI: 10.1039/b901261n

Template-directed synthesis of donor/acceptor [2]catenanes and [2]rotaxanes
journal, January 2008

  • Griffiths, Kirsten E.; Stoddart, J. Fraser
  • Pure and Applied Chemistry, Vol. 80, Issue 3
  • DOI: 10.1351/pac200880030485

Octopus Molecules
journal, December 1974

  • Vögtle, Fritz; Weber, Edwin
  • Angewandte Chemie International Edition in English, Vol. 13, Issue 12
  • DOI: 10.1002/anie.197408141

High-efficiency organic electrophophorescent devices through balance of charge injection
journal, March 2002

  • Jabbour, G. E.; Wang, J. -F.; Peyghambarian, N.
  • Applied Physics Letters, Vol. 80, Issue 11
  • DOI: 10.1063/1.1458687

A Helical Metal−Metal Bonded Chain via the Pt→Ag Dative Bond
journal, January 2001

  • Yamaguchi, Tadashi; Yamazaki, Fumie; Ito, Tasuku
  • Journal of the American Chemical Society, Vol. 123, Issue 4
  • DOI: 10.1021/ja002906a

Dendrimer Chemistry
book, February 2009

Toluene-Sandwiched Trinuclear Copper(I) and Silver(I) Triazolates and Phosphine Adducts of Dinuclear Copper(I) and Silver(I) Triazolates
journal, May 2008

  • Dias, H. V. Rasika; Singh, Shreeyukta; Campana, Charles F.
  • Inorganic Chemistry, Vol. 47, Issue 10
  • DOI: 10.1021/ic800396t

Crystallographic Observation of Dynamic Gas Adsorption Sites and Thermal Expansion in a Breathable Fluorous Metal-Organic Framework
journal, March 2009

  • Yang, Chi; Wang, Xiaoping; Omary, Mohammad A.
  • Angewandte Chemie International Edition, Vol. 48, Issue 14
  • DOI: 10.1002/anie.200804739

Metal Azolate Frameworks: From Crystal Engineering to Functional Materials
journal, September 2011

  • Zhang, Jie-Peng; Zhang, Yue-Biao; Lin, Jian-Bin
  • Chemical Reviews, Vol. 112, Issue 2
  • DOI: 10.1021/cr200139g

Fluorous Pores in Coordination Networks
journal, October 2009

  • Jang, Minsul; Yamaguchi, Takumi; Ohara, Kazuaki
  • Chemistry - An Asian Journal, Vol. 4, Issue 10
  • DOI: 10.1002/asia.200900293

Krakenmoleküle
journal, December 1974

Supramolecular triangular and linear arrays of metal–radical solids using pyrazolato-silver( i ) motifs
journal, January 2004

  • Yamada, Susumu; Ishida, Takayuki; Nogami, Takashi
  • Dalton Trans., Issue 6
  • DOI: 10.1039/B312406A

Meniscus-climbing insects
journal, September 2005

Singlet–singlet excited-state absorption and triplet–triplet absorption of meso-tetraphenylporphine
journal, April 2000

First metal-encapsulating star polysulfoxide incorporating 2-amino-1,3,4-thiadiazole
journal, January 1997

  • Yang, Chi; Zhou, Qin-Hai; Yang, Chi
  • Chemical Communications, Issue 21
  • DOI: 10.1039/a703677i

Luminescence enhancement and tuning via multiple cooperative supramolecular interactions in an ion-paired multinuclear complex
journal, January 2011

  • Yang, Chi; Elbjeirami, Oussama; Gamage, Chammi S. Palehepitiya
  • Chemical Communications, Vol. 47, Issue 26
  • DOI: 10.1039/c1cc11161b

Extrafluorescent electroluminescence in organic light-emitting devices
journal, April 2007

  • Segal, M.; Singh, M.; Rivoire, K.
  • Nature Materials, Vol. 6, Issue 5
  • DOI: 10.1038/nmat1885

Funktionalisierter Koordinationsraum in metall-organischen Gerüsten
journal, October 2008

Solvothermal in Situ Metal/Ligand Reactions:  A New Bridge between Coordination Chemistry and Organic Synthetic Chemistry
journal, February 2007

  • Chen, Xiao-Ming; Tong, Ming-Liang
  • Accounts of Chemical Research, Vol. 40, Issue 2
  • DOI: 10.1021/ar068084p

Flexible Coordination Networks with Fluorinated Backbones. Remarkable Ability for Induced-Fit Enclathration of Organic Molecules
journal, March 2000

  • Kasai, Kayoko; Aoyagi, Masaru; Fujita, Makoto
  • Journal of the American Chemical Society, Vol. 122, Issue 9
  • DOI: 10.1021/ja992553j

Fluorous Nanodroplets Structurally Confined in an Organopalladium Sphere
journal, September 2006

Photoconductive Liquid-Crystalline Derivatives of 6-Oxoverdazyl
journal, January 2012

  • Jankowiak, Aleksandra; Pociecha, Damian; Szczytko, Jacek
  • Journal of the American Chemical Society, Vol. 134, Issue 5
  • DOI: 10.1021/ja209467h

Highly efficient phosphorescent emission from organic electroluminescent devices
journal, September 1998

  • Baldo, M. A.; O'Brien, D. F.; You, Y.
  • Nature, Vol. 395, Issue 6698, p. 151-154
  • DOI: 10.1038/25954

Fluorous Metal–Organic Frameworks with Superior Adsorption and Hydrophobic Properties toward Oil Spill Cleanup and Hydrocarbon Storage
journal, November 2011

  • Yang, Chi; Kaipa, Ushasree; Mather, Qian Zhang
  • Journal of the American Chemical Society, Vol. 133, Issue 45, p. 18094-18097
  • DOI: 10.1021/ja208408n

Supramolecular Chain Assemblies Formed by Interaction of a π Molecular Acid Complex of Mercury with π-Base Trinuclear Gold Complexes
journal, November 2000

  • Burini, Alfredo; Fackler,, John P.; Galassi, Rossana
  • Journal of the American Chemical Society, Vol. 122, Issue 45
  • DOI: 10.1021/ja0024690

Remarkably Simple Fabrication of Superhydrophobic Surfaces Using Electroless Galvanic Deposition
journal, February 2007

  • Larmour, Iain A.; Bell, Steven E. J.; Saunders, Graham C.
  • Angewandte Chemie, Vol. 119, Issue 10
  • DOI: 10.1002/ange.200604596

Self-assembly of Ligands Designed for the Building of a New Type of [2 × 2] Metallic Grid. Anion Encapsulation and Diffusion NMR Spectroscopy
journal, January 2008

  • Manzano, Blanca R.; Jalón, Félix A.; Ortiz, Isabel M.
  • Inorganic Chemistry, Vol. 47, Issue 2
  • DOI: 10.1021/ic701117a

Stacked Platinum Complexes of the Magnus’ Salt Type Inside a Coordination Cage
journal, January 2012

  • Clever, Guido H.; Kawamura, Wataru; Tashiro, Shohei
  • Angewandte Chemie, Vol. 124, Issue 11
  • DOI: 10.1002/ange.201108197

High-efficiency fluorescent organic light-emitting devices using a phosphorescent sensitizer
journal, February 2000

  • Baldo, M. A.; Thompson, M. E.; Forrest, S. R.
  • Nature, Vol. 403, Issue 6771
  • DOI: 10.1038/35001541

Exceptionally Stable, Hollow Tubular Metal−Organic Architectures:  Synthesis, Characterization, and Solid-State Transformation Study
journal, March 2004

  • Su, Cheng-Yong; Goforth, Andrea M.; Smith, Mark D.
  • Journal of the American Chemical Society, Vol. 126, Issue 11
  • DOI: 10.1021/ja039022m

Organonitrile ligated silver complexes with perfluorinated weakly coordinating anions and their catalytic application for coupling reactions
journal, January 2005

  • Zhang, Yanmei; Santos, Ana M.; Herdtweck, Eberhardt
  • New J. Chem., Vol. 29, Issue 2
  • DOI: 10.1039/B414060E

Crystallographic Observation of Dynamic Gas Adsorption Sites and Thermal Expansion in a Breathable Fluorous Metal-Organic Framework
journal, March 2009

  • Yang, Chi; Wang, Xiaoping; Omary, Mohammad A.
  • Angewandte Chemie, Vol. 121, Issue 14
  • DOI: 10.1002/ange.200804739

Dendrimer Chemistry
book, May 2020

  • Malkoch, Michael; García Gallego, Sandra
  • Monographs in Supramolecular Chemistry
  • DOI: 10.1039/9781788012904
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