A Modular Class of Fluorescent Difluoroboranes: Synthesis, Structure, Optical Properties, Theoretical Calculations and Applications for Biological Imaging

Abstract

Ten borylated bipyridines (BOBIPYs) have been synthesized and selected structural modifications have been made that allow useful structure-optical property relationships to be gathered. These systems have been further investigated using DFT calculations and spectroscopic measurements, showing blue to green fluorescence with quantum yields up to 41%. They allow full mapping of the structure to determine where selected functionalities can be implemented, to tune the optical properties or to incorporate linking groups. The best derivative was thus functionalised with an alkyne linker, which would enable further applications through click chemistry and in this optic, the stability of the fluorophores has been evaluated.

Cyanine‐Like Boronic Acid‐Derived Salicylidenehydrazone Complexes (Cy‐BASHY) for Bioimaging Applications

“…Fluorescent dyes that operate in complex chemical environments and under physiological conditions are powerful tools to interrogate biological systems in imaging and sensing experiments [1–3] . The wide application of xanthene dyes, coumarins, boron dipyrromethene (Bodipy) dyes, or alternative organoboron dyes for these purposes substantiate this claim [1, 4–11] . In this context, the archetypal class of cyanine dyes [12–14] has received focused attention.…”

Azabora[5]helicene Charge‐Transfer Dyes Show Efficient and Spectrally Variable Circularly Polarized Luminescence

“…[18] Much effort has been dedicated to the development of synthetically flexible platforms which enablet he photophysical fine-tuning of the dyes. [3,[9][10][11][19][20][21][22][23][24][25][26][27] As parto fo ur own research program we have developed borylated arylisoquinoline (BAI) dyes,w hich in their N,C-chelate variant are strongly emitting, solvatochromic, and two-photon-absorbing charge-transfer fluorophores with applicationp otentiali nb ioimaging. [9,10,28] With the idea to further enricht he photophysicso ft his fascinating platform we have built on their biaryl structure,w hich providesameanst oa rrive at dyes with helical chirality and the correspondingo bservation of interesting chiropticalp roperties, including the detection of circularly polarized luminescence (CPL).…”

Regioselective Cyanation of Six‐Membered N‐Heteroaromatic Compounds Under Metal‐, Activator‐, Base‐ and Solvent‐Free Conditions

“…[40] 2a was readily obtainable and could be easily converted to the 2,4-diamino-1,3,5-triazine derivative 14, an important precursor for anticancer activity. [40] 2a was readily obtainable and could be easily converted to the 2,4-diamino-1,3,5-triazine derivative 14, an important precursor for anticancer activity.…”