Spectroscopic and photophysicochemical properties of zinc(II) phthalocyanine substituted with benzenesulfonamide units containing schiff base

IF 1.3 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Main Group Chemistry Pub Date : 2022-11-22 DOI:10.3233/mgc-220067

Gülen Atiye Öncül, Ö. Öztürk, M. Pişkin

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引用次数: 0

Abstract

In this study, compounds (E)-4-((5-bromo-2-hydroxy-3-methoxybenzylidene)amino)-N-(pyridin-2-yl)benzenesul-fonamide 1, (E)-4-((5-bromo-2-(3,4-dicyanophenoxy)-3-methoxybenzylidene)amino)-N-(pyridin-2-yl)benzenesulfonamide 2 and, complex 2(3),9(10),16(17),23(24)-tetra-[(E)-4-((5-bromo-3-methoxy-2-(λ 1-oxidanyl)benzylidene)amino)-N-(pyridine-2-yl)benzenesulfonamide]phthalocyaninato zinc(II) 3 were synthesized for the first time. Their structures (1 –3) were characterized by spectroscopic methods such as FTIR, 1H NMR,13C NMR, UV–vis, MALDI-TOF mass spectra and elemental analysis. The spectroscopic, aggregation, photophysical and photochemical properties of zinc(II) phthalocyanine 3 in dimethyl sulfoxide were investigated and the effects on the above-mentioned properties were reported as a result of the presence of benzenesulfonamide derivatives containing different bioactive groups, in their peripheral positions. In addition, its above-mentioned properties were also reported by comparing different species with those of their substituted and/or unsubstituted counterparts. The zinc(II) phthalocyanine 3 can be a potential photosensitizer candidate in photodynamic therapy, which is an effective alternative therapy in cancer treatment, due to its good solubility in commonly known solvents and monomeric species, as well as its adequate and favorable fluorescence, singlet oxygen production and photostability.

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含席夫碱的苯磺酰胺单元取代酞菁锌的光谱和光物理化学性质

本文首次合成了化合物(E)-4-(5-溴-2-羟基-3-甲氧基苄基)氨基)- n-(吡啶-2-基)苯磺酰胺1、(E)-4-(5-溴-2-(3,4-二氰苯氧基)-3-甲氧基苄基)氨基)- n-(吡啶-2-基)苯磺酰胺2和配合物2(3)、9(10)、16(17)、23(24)-四-[(E)-4-((5-溴-3-甲氧基-2-(λ 1-氧化基)苄基)氨基)- n-(吡啶-2-基)苯磺酰胺]酞菁锌(II) 3。采用FTIR、1H NMR、13C NMR、UV-vis、MALDI-TOF质谱和元素分析等方法对其结构(1 -3)进行了表征。研究了酞菁锌(II) 3在二甲亚砜中的光谱、聚集、光物理和光化学性质，并报道了含有不同生物活性基团的苯磺酰胺衍生物在其外围位置的存在对上述性质的影响。此外，通过与取代和/或未取代对应物的比较，还报道了其上述性质。锌(II)酞菁3由于其在已知溶剂和单体中具有良好的溶解度，且具有充足的荧光、单线态产氧和光稳定性，可作为潜在的光敏剂用于光动力治疗，是癌症治疗的有效替代疗法。

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来源期刊

Main Group Chemistry 化学-化学综合

CiteScore

2.00

自引率

26.70%

发文量

审稿时长

>12 weeks

期刊介绍： Main Group Chemistry is intended to be a primary resource for all chemistry, engineering, biological, and materials researchers in both academia and in industry with an interest in the elements from the groups 1, 2, 12–18, lanthanides and actinides. The journal is committed to maintaining a high standard for its publications. This will be ensured by a rigorous peer-review process with most articles being reviewed by at least one editorial board member. Additionally, all manuscripts will be proofread and corrected by a dedicated copy editor located at the University of Kentucky.