期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 23, 期 8, 页码 1795-1804出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604978
关键词
azomethine; nitrogen; fluorescence; intramolecular charge transfer; phthalocyanines; sensors
资金
- Czech Science Foundation [14- 02165P]
- Charles University in Prague [SVV 260 291]
- Minnesota Supercomputing Institute
- U of M
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1464711] Funding Source: National Science Foundation
A unique combination of two independent mechanisms of fluorescence quenching, namely intramolecular charge transfer (ICT) from a peripheral donor and protonation of azomethine nitrogen atoms in zinc tetrapyrazinoporphyrazines (TPyzPz), provides a new possibility for sensing pH in a specific range. The pH selectivity was controlled by the different basicities of the donor for ICT (dimethylaminoaryl), which was connected to the macrocycle by pi-extended linkers of different lengths. ICT and protonation have been studied in detail by photophysical, spectral (UV/Vis and MCD spectra), and electrochemical measurements, and further supported by theoretical calculations (DFT, TDDFT). The pH-sensing properties of the TPyzPzs have been investigated in THF and in water after anchoring the TPyzPzs to liposomes. The salient pK(a) values were around 1.3 (azomethine nitrogen) and 2.29-4.76 ( donor for ICT). The lead indicators (sensing over a pH range of 1.0-2.5) with fairly steep sensing profiles exhibited increases in fluorescence between the OFF/ON states of more than 20-fold and strong absorption in the red region (Q-band maximum >650 nm, epsilon approximate to 2 x 10(6) m-(1) cm (-1)).
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