Spectroscopic characterization of C-4 substituted 3,5-dichloro-4H-1,2,6-thiadiazines
Date
2015Author
Theodorou, E.Ioannidou, Heraklidia A.
Ioannou, Theodosia A.
Kalogirou, Andreas S.
Constantinides, Christos P.
Manoli, Maria
Koutentis, Panayiotis Andreas
Hayes, Sophia C.
ISSN
2046-2069Source
RSC AdvancesVolume
5Issue
24Pages
18471-18481Google Scholar check
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Metadata
Show full item recordAbstract
Three 3,5-dichloro-4H-1,2,6-thiadiazines, which differ according to the electron withdrawing nature of their substituent at C-4: (a) 3,5-dichloro-4-methylene-4H-1,2,6-thiadiazine (5a), (b) 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (5b) and (c) 2-(3,5-dichloro-4H-1,2,6-thiadiazin-4-ylidene)malononitrile (5c), are characterized using resonance Raman (RR), absorption (UV/vis) and photoluminescence (PL) spectroscopies. These weakly aromatic and electron-deficient heterocycles are potential components as acceptors in donor-acceptor systems for organic electronics. Experimental results, which include the synthesis, characterization and single crystal X-ray structure of 3,5-dichloro-4-methylene-4H-1,2,6-thiadiazine (5a), combined with theoretical calculations of their orbitals and vibrational frequencies, provide an understanding of the optical properties, on the basis of molecular geometry and electron distribution. © The Royal Society of Chemistry 2015.