Synthesis, X‐ray Structure, Spectral and Electrochemical Properties of Aza‐BODIPY‐Metal Dipyrrinyl Conjugates. Issue 30 (23rd October 2017)

• Record Type: Journal Article
• Authors: Kumar, Ankit; Ravikanth, Mangalampalli
• Is Part Of: ChemistrySelect. Volume 2:Issue 30(2017)
• Page Start: 9663
• Page End: 9669
• Publication Date: 2017-10-23
• Subjects: AzaBODIPY -- Chromophores -- cyclic voltammetry -- Fluorescence -- Metal dipyrrin; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201702060
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Aza‐boron‐dipyromethene (aza‐BODIPY) derivative4 ( β ‐Dipyrrinyl aza‐BODIPY) was prepared readily from β ‐formyl aza‐BODIPY and used as a key synthon for the preparation of aza‐BODIPY‐metal dipyrrinyl conjugates. Three aza‐BODIPY‐metal dipyrrinyl conjugates (M=Re(I), Ni(II) and Zn(II)) were prepared by treating β ‐dipyrrinyl aza‐BODIPY with appropriate metal salts at reflux temperature followed by column chromatographic purification. The aza‐BODIPY‐metal dipyrrinyl conjugates were freely soluble in common organic solvents and stable in solid and in solution states. The conjugates were characterized in detail by HR‐MS, 1D & 2D NMR, absorption, electrochemical and fluorescence techniques and the structure of the one of the conjugate was deduced by X‐ray crystallography. The X‐ray structure revealed that 1, 3, 5, 7‐tetratolyl aza‐BODIPY and Re(I) dipyrrinyl moieties in aza‐BODIPY−Re(I) dipyrrinyl conjugate were perpendicular to each other with a dihedral angle of 89°. The absorption and electrochemical studies revealed that the aza‐BODIPY and dipyrrinyl moieties in conjugates interact weakly and retain their individual properties. The aza‐BODIPY‐metal dipyrrinyl conjugates were very weakly fluorescent. Abstract : The β ‐dipyrrinyl substituted aza‐BODIPY was used to prepare three different aza‐BODIPY‐metal dipyrrinyl conjugates and studied their structure, spectral and electrochemical properties. The X‐ray structure revealed that aza‐BODIPY and Re(I) dipyrrinyl moieties in aza‐BODIPY−Re(I) dipyrrinyl conjugate were perpendicular to each other. The spectral and electrochemical studies indicates that in conjugates, the aza‐BODIPY and metal dipyrrinyl moieties interact weakly and retain their individual characteristic features.