1, 7‐Difluorophore‐Substituted AzaBODIPYs. Issue 2 (16th January 2018)

• Record Type: Journal Article
• Authors: Koch, Angira; Ravikanth, Mangalampalli
• Is Part Of: European journal of organic chemistry. Issue 2(2018)
• Page Start: 228
• Page End: 234
• Publication Date: 2018-01-16
• Subjects: Functional organic materials -- Aza‐BODIPYs -- Photophysics -- Fluorophores -- Cyclic voltammetry -- Energy transfer; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701396
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Four different 1, 7‐disubstituted azaBODIPYs containing fluorophores such as naphthalene, anthracene, and pyrene were synthesized over multiple steps involving aldol condensation, Michael addition, dipyrromethene formation, and BF2 complexation. All of these steps were optimized, and the target 1, 7‐difluoro‐substituted azaBODIPYs along with other intermediate compounds were thoroughly characterized by HRMS and 1D and 2D NMR spectroscopy. Absorption and electrochemical studies indicated a strong interaction between the fluorophores and the azaBODIPY moieties in compounds1–4 . Fluorescence studies revealed that 1, 7‐disubstituted azaBODIPYs with naphthalene and pyrene fluorophores were fluorescent and that singlet–singlet energy transfer from the fluorophores to the azaBODIPY moiety was possible, whereas 1, 7‐dianthracenyl‐substituted azaBODIPY was completely nonfluorescent owing to efficient photoinduced electron transfer between the anthracene and azaBODIPY moieties. Abstract : AzaBODIPYs appended with different fluorophores such as naphthalene, anthracene, and pyrene at the 1, 7‐positions are synthesized over multiple steps and their photophysical and electrochemical properties are studied.