In:
European Journal of Organic Chemistry, Wiley, Vol. 2015, No. 3 ( 2015-01), p. 596-604
Abstract:
A series of low‐symmetry Zn II , Mg II , and metal‐free porphyrazine derivatives with one 1,2,5‐chalcogenadiazole ring (with S, Se or Te) and three pyrazines bearing tert ‐butylsulfanyls were synthesized. The absorption maxima of Zn II complexes lay at 660, 674, and 707 nm for S, Se, and Te, respectively, indicating increasing contribution of the 1,2,5‐chalcogenadiazole rings to the π‐electronic system. Photophysical studies revealed that introduction of Se as a chalcogen and Zn II as a central metal causes an increase in the singlet oxygen quantum yield, reaching a value of 0.81, whereas the combination of S and Mg II gives only 0.39. This takes place on the account of the fluorescence quantum yields that differ significantly from 0.072 (Zn II +Se) to 0.51 (Mg II +S). These results demonstrated the two‐dimensional heavy atom effect combining the role of the chalcogen (first dimension) as well as the central metal (second dimension). Attempts to prepare oxygen‐containing isologues led to the formation of an unexpected side product.
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2015.3
DOI:
10.1002/ejoc.201403329
Language:
English
Publisher:
Wiley
Publication Date:
2015
detail.hit.zdb_id:
1475010-7
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