Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 5, Pages 2569-2579Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02525
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Funding
- European Research Council [ERC-2017-StG-757733]
- Swedish Research Council [2016-03354]
- Knut and Alice Wallenberg Foundation [KAW 2017.0192]
- Swedish Research Council [2016-03354] Funding Source: Swedish Research Council
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This study provides a photophysical evaluation of BODIPY and aza-BODIPY derivatives, leading to a deeper understanding of the structure-function relationship and facilitating the design of tailor-made molecules in the future.
In the field of fluorescent dyes, difluoroboron-dipyrromethenes (BODIPY) have a highly respected position. To predict their photophysical properties prior to synthesis and therefore to successfully design molecules specifically for one's needs, a solid structure-function understanding based on experimental observations is vital. This work delivers a photophysical evaluation of BODIPY and aza-BODIPY derivatives equipped with different electron-withdrawing/-donating substituents. Using combinatorial chemistry, pyrroles substituted with electron-donating/-withdrawing substituents were condensed together in two different manners, thus providing two sets of molecules. The only difference between the two sets is the bridging unit providing a so far lacking comparison between BODIPYs and aza-BODIPYs structural homologues. Replacing the meso-methine bridge with an aza-N bridge results in a red-shifted transition and considerably different, temperature-activated, excited-state relaxation pathways. The effect of electron-donating units on the absorption but not emission for BODIPYs was suppressed compared to aza-BODIPYs. This result could be evident in a substitution pattern-dependent Stokes shift. The outlook of this study is a deeper understanding of the structure-optics relationship of the (aza)-BODIPY-dye class, leading to an improvement in the de novo design of tailor-made molecules for future applications.
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