NDLI: Efficient Complexation of Pyrrole-Bridged Dizinc(II) Bisporphyrin with Fluorescent Probe Pyrene: Synthesis, Structure, and Photoinduced Singlet–Singlet Energy Transfer

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Efficient Complexation of Pyrrole-Bridged Dizinc(II) Bisporphyrin with Fluorescent Probe Pyrene: Synthesis, Structure, and Photoinduced Singlet–Singlet Energy Transfer

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Efficient Complexation of Pyrrole-Bridged Dizinc(II) Bisporphyrin with Fluorescent Probe Pyrene: Synthesis, Structure, and Photoinduced Singlet–Singlet Energy Transfer

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Chaudhary, Arvind Rath, Sankar Prasad
Description	Author Affiliation: Chaudhary A ( Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur-208016, India.)
Abstract	A diethylpyrrole-bridged dizinc(II) bisporphyrin $(Zn_{2}DEP)$ is reported that encapsulates fluorescent probe pyrene molecules through strong π–π interactions, which can relay information about the chemical environment in the interior of the host–guest supramolecular assembly. X-ray structures of both $Zn_{2}DEP$ and the encapsulated pyrene complex are reported, which provides a rare opportunity to investigate the structural changes upon guest binding. A comparative structural analysis demonstrated the exceptional ability of this bisporphyrin platform to open its binding pocket for pyrene encapsulation by a vertical displacement of more than 2.45 Å, although both $Zn_{2}DEP$ and the pyrene complex have nearly parallel porphyrin ring orientations. The $^{1}H NMR$ spectrum of the encapsulated pyrene complex in solution shows the upfield shifts of the pyrene protons due to a strong ring current effect, which demonstrates the retention of the solid-state structure in solution. To further assess the extent to which pyrene guests remain encapsulated in solution, a known fluorescence quencher, dimethylaniline, was added to the host–guest assembly, which shows no exciplex formation for days in nonpolar solvents. Thus, the assembly also retained the structural integrity in solution for a long time. The association constant $(K_{asso})$ for such a complexation process in solution was observed to be $1.78×10^{5} M^{−2}$ for 1:2 binding. Steady-state fluorescence and lifetime studies indicate significant photoinduced singlet–singlet energy transformation from the excited state of pyrene to zinc bisporphyrin.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	41
Volume Number	17
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2011-10-04
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Fluorescent Dyes Chemistry Organometallic Compounds Porphyrins Pyrenes Pyrroles Zinc Crystallography, X-Ray Energy Transfer Magnetic Resonance Spectroscopy Molecular Structure Chemical Synthesis Photochemistry Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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