Tuning the π-bridge of quadrupolar triarylborane chromophores for one- and two-photon excited fluorescence imaging of lysosomes in live cells

Abstract

The tetracationic diketopyrrolopyrrole compound 5M exhibits a σ2 value of 4560 GM at 740 nm.

A Quadrupolar Bis‐Triarylborane Chromophore as a Fluorimetric and Chirooptic Probe for Simultaneous and Selective Sensing of DNA, RNA and Proteins

“…We recently reported the water-soluble and stable cationic bis-triarylborane derivative 1 as an ew fluorophore applicable for one-and two-photon excited fluorescence imaging in cells. [3] Given that only af ew examples of water-soluble triarylboranes have been reported to date, [4][5][6][7][8][9][10][11][12][13] such borane-based chromophores could be considered to be novel fluorophores for biochemical applications;t hey are already widely used in nonlinearo ptical materials, organic electronics, organic lightemitting diodes or anion sensors. [14][15][16][17][18][19][20][21][22] However,f luorescence of 1 only enabled intracellularl ocalisation of ad ye, but did not allow fort he determination of at argeted biomacromolecule (for example, protein or DNA or RNA).…”

Stereospecific Synthesis and Photophysical Properties of Propeller‐Shaped C90H48PAH

“…Previously,i tw as observed that the solventp olarity has a large influence on the two photon cross-section value. [22] Therefore, the two-photon absorption (TPA) cross-section of (M,M,M,P,P,P)-3 was measured in two solvents with al arge differencei np olarity,T HF,a nd toluene, via two-photoni nduced fluorescencer elative spectroscopict echnique ( Figure 6). The observedo verlap between one-and two-photon absorption spectra is,o no ne hand, attributed to the noncentrosymmetric molecule, in which the parity selection rule does not hold.…”

Insights into the Optical Properties of Triarylboranes with Strongly Electron‐Accepting Bis(fluoromesityl)boryl Groups: when Theory Meets Experiment

“…A large number of air-stable conjugated three-coordinate organoboron compounds have been synthesized over the last few decades [1][2][3][4][5][6][7][8] for various applications, particularly in linear [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24] and nonlinear [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39] optics, electro-optic devices, [40][41][42] anion sensors, [43,44] cell imaging, [45][46][47][48] etc. The boron center in these species possesses an empty p-orbital and can thus serve as a strong π-acceptor following photo-excitation, or as a readily reducible center.…”

“…Alternative bulky groups with higher electron affinities should enhance acceptor strength while maintaining or even enhancing the desired chemical stability of the systems. [6,12,28,[36][37][38][57][58][59][60][61][62][63][64][65][66][67] Exploiting this favorable property, some of us recently reported a series of air-stable bis (fluoromesityl)boryl ((FMes) 2 B) derivatives, namely compounds 1-3 (Scheme 1) with different electron-donating groups for comparison, i. e., phenyl, 4-tert-butylphenyl and 4-N,N-diphenylaminophenyl, respectively, attached to the electron acceptor group (FMes) 2 B through BÀ C bonds. [12] Comparison of these (FMes) 2 B-containing donor-acceptor compounds with compound 4, which contains a (Mes) 2 B group (Scheme 1), confirms that (FMes) 2 B is a much stronger acceptor, leading to: (i) a larger quinoidal distortion in the ground state structure; (ii) significantly red-shifted emission in solution and in the solid state; (iii) stronger emission solvatochromism; and (iv) significantly lower reduction potentials.…”