The Effect of Substituent on Photophysical Properties of Some 4-(2-Substitutedhydrazinyl)Benzenesulfonamides Derivatives

Erzincan Üniversitesi Fen Bilimleri Enstitüsü Dergisi 2016, 9(3), 164-171 Araştırma Makalesi Erzincan University Journal of Science and Technology 2016, 9(3), 164-171 Research Article The Effect of Substituent on Photophysical Properties of Some 4-(2Substitutedhydrazinyl)Benzenesulfonamides Derivatives Ebru BOZKURT1*, Halise İnci GÜL2, Kübra Gizem YILDIZTEKİN3, Hilal BAKKAL4 1Program of Occupational Health and Safety, Erzurum Vocational Training School, Ataturk University, Erzurum, Turkey 2Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, Erzurum, Turkey 3Department of Pharmaceutical Toxicology, Faculty of Pharmacy, Erzincan University, Erzincan, Turkey 4Researh Project Students, Faculty of Pharmacy, Ataturk University, Erzurum, Turkey (Geliş Tarihi/Received: 21.04.2016, Kabul Tarihi/Accepted: 23.06.2016) ABSTRACT In this study, the effect of substituent on the photo-physical properties of some sulfonamide derivatives; 4-(2-substitutedhydrazinyl)benzenesulfonamides in which aryl part was changed as phenyl (S1), 4-methylphenyl (S2), 4-chlorophenyl (S3), 4-fluorophenyl (S4), 4-bromophenyl (S5), 4methoxyphenyl (S6), 4-nitrophenyl (S7), 2-thienly (S8) and 2-furyl (S9) were examined in DMSO: H2O (1:1 v/v) solution by using UV-Vis absorption, steady-state and time-resolved fluorescence spectroscopy techniques. It was determined that the sulfonamide derivatives studied exhibited fluorescence property at the blue-green region without exception. Their fluorescence properties were varied by changing the aryl part. The photophysical parameters of the sulfonamide derivatives were calculated in DMSO: H2O (1:1 v/v) solution from the spectroscopic data. Consequently, these molecules having biological activity were spectroscopically characterized, and the effect of substituent on their photo-physical properties was examined. Keywords: Substituent effect; absorption; fluorescence; photo-physical parameters. Bazı 4-(2-Substiehidrazin)Benzen Sülfonamit Türevlerinin Fotofiziksel Özellikleri Üzerine Sübtitüent Etkisi ÖZET Bu çalışmada aril grubu, fenil (S1), 4-metilfenil (S2), 4-klorofenil (S3), 4-florofenil (S4), 4-bromofenil (S5), 4-metoksifenil (S6), 4-nitrofenil (S7), 2-thienly (S8) ve 2-furil (S9) olarak değiştirilen bazı 4-(2substiehidrazin)benzen sülfonamit türevlerinin DMSO: H2O (1:1 v/v) çözeltisi içindeki fotofiziksel özellikleri üzerine sübtitüent etkisi UV-gör. absorpsiyon, durgun-hal ve zamana-bağlı floresans spektroskopisi teknikleri kullanılarak incelenmiştir. Çalışılan sülfonamid türevlerinin tamamının mavi-yeşil bölgede floresans özellik gösterdikleri belirlenmiştir. Bileşiklerin floresans özelliklerinin, aril grubunun değişmesiyle değiştiği gözlenmiştir. Spektroskopik veriler yardımıyla sülfonamit türevlerinin DMSO: H2O (1:1 v/v) çözeltisi içindeki fotofiziksel parametreleri de hesaplanmıştır. Sonuç olarak, biyolojik aktiviteye sahip olan bu moleküller spektroskopik olarak karakterize edilmiş ve bunların fotofiziksel özelliklerine sübstitüent etkisi incelenmiştir. Anahtar Kelimeler: Sübstitüent etkisi; absorpsiyon; floresans; fotofiziksel parametreler. ISSN: 1307-9085 e-ISSN: 2149-4584 *Correspondence to: DOI: 10.18185/eufbed.78181 Erzincan Univ J Sci Tech 9(3), 2016, 164-171 Bozkurt ve Diğerleri 1. Introduction shift (Zollinger, 2003). Consequently, the Sulfonamides are known as powerful fluorescence properties of these type organic carbonic anhydrase (CA) inhibitors (Hu et compounds can be successfully modified al., 2015). However, sulfonamide derivatives with attaching appropriate substituents. have wide range of biological activities such as antibacterial, inflammatory antidiabetic, and antitumor antiactivities (Khazalpour & Nematollahi, 2015; Reddy et al., 2015; Zani & Vicini, 1998; Zhang, Lin, Liu, & Lin, 2015). They are used widely in the medicinal chemistry significant because pharmacological of these properties. Additionally, these compounds are also involved in spectroscopic studies (Gökoğlu & Yılmaz, 2014; Hu, et al., 2015; Özturk, Förstel, Ergun, Alp, & Rettig, 2008; Suganya & Kabilan, 2004; Yu, Liu, Guo, & Yang, 2013). Recently, an investigation of the changes in the photo-physical properties of sulfonamide derivatives depending on the attached substituent group has consisted an important study area (Zakerhamidi, AhmadiKandjani, Moghadam, Ortyl, & Kucharski, In the present study, it was reported the effect of substituent on the photo-physical properties of some sulfonamide derivatives having the chemical structure of 4-(2substitutedhydrazinyl)benzenesulfonamides. Ketones used for the synthesis of S1-S9 were changed as acetophenone derivatives in S1S7 having electron donating or attracting substituent at 4-position of phenyl ring or 2acethylthiophene in S8 or 2-acethylfuran in S9 to observe how the differences in substituent on phenyl ring direct the photophysical properties of the compounds studied or how the differences in aryl moiety (such as phenyl, 2-thienyl, 2-furyl) direct the same properties. The absorption and fluorescence properties of the compounds were spectroscopically characterized as well as their photo-physical parameters. 2011, 2012). In this regard, the changes on the absorption and emission maxima and 2. Materials and Methods quantum yields of the compounds can be occurred by the effect of substituents or 2.1. Chemicals solvents Methanol (Fu & Wang, 2008; Karcı, (MeOH, Sigma), dimethyl Demirçalı, Şener, & Tilki, 2006; Raposo, sulfoxide (DMSO, Sigma), quinine sulfate Sousa, Fonseca, Yazdanbakhsh Zollinger, & 2003). Kirsch, 2005; (Fluka) and H2SO4 (Sigma) were purchased Mohammadi, 2009; and used without further purification. The & The absorption (or stock solution of all compounds was fluorescence) maximum shifted to longer prepared in MeOH. A certain amount of wavelength is called as red or bathochromic fresh probe samples in DMSO: H2O (1:1 v/v) shift, while their shifting towards shorten solution was prepared from this stock wavelength is called as blue or hypsochromic solution 165 by diluting process. For all Erzincan Univ J Sci Tech 9(3), 2016, 164-171 Bozkurt ve Diğerleri measurements, the concentrations of the The fluorescence quantum yields of the compounds were 1.0x10-5 samples were calculated through the Parker- experiments were performed M. All at the room Rees equation: −ODr D n2 ∅s = ∅r ( s⁄D ) ( s⁄n2 ) [(1 − 10 ⁄1 − 10−ODs )] r r temperature. (1) where D is the integrated area under the 2.2. Equipment corrected fluorescence spectrum, n is the The UV-Vis absorption and fluorescence refractive index of the solution, and OD is the spectra of the samples were recorded with optical density at the excitation wavelength Perkin (λex= 330 nm). The subscripts s and r refer to Elmer Lambda 35 and Shimadzu spectrophotometer 5301PC UV/VIS RF- spectrofluorophotometer, respectively. The (...truncated)