Measuring Cumulative Exposure to Oxygen with a Diphenylphosphine-Alkyl Naphthaleneimide Luminescence Turn-On Dyad

2‐(2‐Diphenylphosphanylethyl)benzo[de]isoquinoline‐1,3‐dione is a poorly luminescent, photoinduced‐electron‐transfer (PET) dyad, NI‐(Ph)2P:, in which the luminescence of its naphthaleneimide (NI) part is quenched by the lone‐pair electrons of the phosphorus atom of the (Ph)2P: group. Photoinduced ox...

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Bibliographic Details
Published in:Chemistry : a European journal 2015-08, Vol.21 (32), p.11531-11537
Main Authors: Shritz, Rozalia, Shapira, Reut, Borzin, Elena, Tumanskii, Boris, Reichstein, Werner, Meichner, Christoph, Schwaiger, Florian, Reichstein, Paul M., Kreyenschmidt, Judith, Haarer, Dietrich, Kador, Lothar, Eichen, Yoav
Format: Article
Language:English
Subjects:
analytical methods
Chemistry
electron transfer
Exposure
Flexibility
Luminescence
Mathematical analysis
Monitoring
Nickel
Oxidation
Oxygen
Phosphines
Phosphorus
photochemistry
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Summary:2‐(2‐Diphenylphosphanylethyl)benzo[de]isoquinoline‐1,3‐dione is a poorly luminescent, photoinduced‐electron‐transfer (PET) dyad, NI‐(Ph)2P:, in which the luminescence of its naphthaleneimide (NI) part is quenched by the lone‐pair electrons of the phosphorus atom of the (Ph)2P: group. Photoinduced oxidation of (Ph)2P: to (Ph)2PO by molecular oxygen regenerates the luminescence of the NI group, because the oxidized form (Ph)2PO does not serve as a quencher to the NI system. The oxidation of (Ph)2P: is thermally inaccessible. The NI‐(Ph)2P: system was applied to monitoring the cumulative exposure of oxidation‐sensitive goods to molecular oxygen. The major advantage of this new PET system is that it reacts with oxygen only via the photoinduced channel, which offers the flexibility of monitoring the cumulative exposure to oxygen in different time periods, simply by varying the sampling frequency. Electronic‐energy calculations and optical spectroscopic data revealed that the luminescence turn‐on upon reaction with molecular oxygen relies on a PET mechanism. Lighting up molecular oxygen: The photooxidation‐dependent luminescence turn‐on process of a naphthaleneimide–ethyl diphenyl phosphine dyad was studied with the aim of providing a new means to assess the cumulative exposure of goods to molecular oxygen. The system relies on a photoinduced electron‐transfer (PET) mechanism (see figure) and allows repetitive measurements of the concentration of molecular oxygen over various periods of time.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201500479