Synthesis and Photophysical Properties of Some Rigidized Hepta‐ and Nonamethine Mono‐ and Bis(merocyanines): Ring‐Opening of Quaternized 2‐Methylbenzothiazole
作者： Lilia Viteva , Tzveta Gospodova , Jivka Rashkova , Isaac Abrahams , Iliana Timtcheva
关键词: Polymer chemistry 、 Merocyanine 、 Organic chemistry 、 Nucleophilic addition 、 Methyl group 、 Hofmann elimination 、 Benzothiazole 、 Chemistry 、 Cyclopentene 、 Regioselectivity 、 Diketone
摘要: We have developed a simple and efficient method for the synthesis of rigidized mono- bis-heptamethine merocyanines that contain one methine unit incorporated into cyclopentene framework. The synthetic approach is based on C1/C5 regioselective nucleophilic addition diketone lithium enolates to readily available pentamethine cyanines with inherent rigidity followed by Hofmann elimination reaction. new dyes react easily heterocyclic benzothiazolium compounds containing an activated methyl group. Depending reaction conditions or two reactive centres can be attacked, thus giving access merocyanine derivatives lengthened polymethine chain and/or ramified second unit. X-ray crystallographic analysis reveals heterocycle via sulfur bridge as result opening benzothiazole ring. All were fully characterized 1D 2D NMR spectroscopic techniques (1H, 13C, DEPT, COSY, NOESY, HSQC without decoupling, HMBC). Their photophysical properties been studied correlated solvent polarities. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
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