Synthesis And Properties Of NIR Aza-BODIPY Dyes

Aza-BODIPYs have excellent properties, such as long-wavelengthemission and absorption wavelength, good photostability, sharp andintense absorption, and have found attracted great attentions lately.This thesis is mainly focused on derivation of aza-BODIPY core,through the installation of thiophene rings or phenanthrene rings ontoaza-BODIPY core, to enhance the conjugation of aza-BODIPY core andredshift the spectra further into the NIR range. A series ofolig-aza-BODIPYs have also been prepared starting from theβ-formylation of aza-BODIPY.1. A series of β-thiophene-fused aza-BODIPY(aza-BDTPs)5a-5fhave been synthesized from Hemetsberge reaction, and subsequentbromination, Suzuki reaction and have been characterized via NMR, MSand X-ray diffraction. Spectral properties of these dyes were studied, inwhich a sharp absorption centered at around800nm and a high spectralselectivity have been observed for these highly photostable aza-BDTPs.2. A set of β-phenanthrene-fused aza-BODIPY (aza-BDPTs) D1-D12have been synthesized via Suzuki coupling reaction (to afford2,6-diphenyl-aza-BODIPYs C1-C12) and the subsequent oxidativecoupling with anhydrous ferric chloride starting from the ready-made2,6-dibromo-aza-BODIPYs B1-B9. These novel dyes have been fullycharacterized via NMR, MS and X-ray diffraction. Spectral properties of these dyes were studied, in which a sharp absorption centered at around800nm and a high spectral selectivity have been observed for thesehighlyphotostable aza-BDPTs.3. A set of meso-β directly linked Olig-aza-BODIPYs c1-c6havebeen synthesized and characterized via NMR and X-ray diffractionstarting from the ready-made β-formyl-aza-BODIPYs b1-b2.