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

Chi Yang; Ravi K. Arvapally; Sammer M. Tekarli; Gustavo A. Salazar; Oussama Elbjeirami; Xiaoping Wang; Mohammad A. Omary

doi:10.1002/anie.201411462

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

Chi Yang
, Ravi K. Arvapally
, Sammer M. Tekarli
, Gustavo A. Salazar
, Oussama Elbjeirami
, Xiaoping Wang
, Mohammad A. Omary

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

8 Scopus citations

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–π interactions affords the supramolecular assemblies [1⋅PtOEP] or [1⋅H₂OEP] (2 a), which feature nanoscopic cavities surrounding the upper triangular and lower square cores. The fluorous/organic biphasic configuration of [1⋅PtOEP] 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.

Original language	English
Pages (from-to)	4842-4846
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	16
DOIs	https://doi.org/10.1002/anie.201411462
State	Published - Apr 13 2015

Funding

Support by the U.S. National Science Foundation (CHE-1413641, CHE-0911690, CMMI-0963509, and CHE-0840518) and the Robert A. Welch Foundation (Grant B-1542) is gratefully acknowledged. X.P.W. acknowledges support by the Scientific User Facilities Division, Office of Basic Energy Sciences, U.S. Department of Energy (DE-AC05-00OR22725) managed by UT Battelle, LLC.

Keywords

fluorine
heterocycles
luminescent materials
porphyrins
supramolecular chemistry

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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–π interactions affords the supramolecular assemblies [1⋅PtOEP] or [1⋅H2OEP] (2 a), which feature nanoscopic cavities surrounding the upper triangular and lower square cores. The fluorous/organic biphasic configuration of [1⋅PtOEP] 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.",

keywords = "fluorine, heterocycles, luminescent materials, porphyrins, supramolecular chemistry",

author = "Chi Yang and Arvapally, \{Ravi K.\} and Tekarli, \{Sammer M.\} and Salazar, \{Gustavo A.\} and Oussama Elbjeirami and Xiaoping Wang and Omary, \{Mohammad A.\}",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2015",

month = apr,

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doi = "10.1002/anie.201411462",

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AU - Yang, Chi

AU - Arvapally, Ravi K.

AU - Tekarli, Sammer M.

AU - Salazar, Gustavo A.

AU - Elbjeirami, Oussama

AU - Wang, Xiaoping

AU - Omary, Mohammad A.

PY - 2015/4/13

Y1 - 2015/4/13

N2 - 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–π interactions affords the supramolecular assemblies [1⋅PtOEP] or [1⋅H2OEP] (2 a), which feature nanoscopic cavities surrounding the upper triangular and lower square cores. The fluorous/organic biphasic configuration of [1⋅PtOEP] 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.

AB - 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–π interactions affords the supramolecular assemblies [1⋅PtOEP] or [1⋅H2OEP] (2 a), which feature nanoscopic cavities surrounding the upper triangular and lower square cores. The fluorous/organic biphasic configuration of [1⋅PtOEP] 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.

KW - fluorine

KW - heterocycles

KW - luminescent materials

KW - porphyrins

KW - supramolecular chemistry

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DO - 10.1002/anie.201411462

M3 - Article

AN - SCOPUS:85027951111

SN - 1433-7851

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 16

ER -

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

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