Alkoxy Tetrazine Substitution at a Boron Center: A Strategy for Synthesizing Highly Fluorogenic Hydrophilic Probes

ChemBioChem ◽  
2018 ◽  
Vol 19 (6) ◽  
pp. 530-534 ◽  
Author(s):  
Min Wu ◽  
Xiaoai Wu ◽  
Yayue Wang ◽  
Lei Gu ◽  
Jiao You ◽  
...  
Keyword(s):  
Boron Center

BODIPY Fluorophores for Membrane Potential Imaging

2019 ◽  
Author(s):  
Jenna Franke ◽  
Benjamin Raliski ◽  
Steven Boggess ◽  
Divya Natesan ◽  
Evan Koretsky ◽  
...  
Keyword(s):  
Mammalian Cells ◽  
Water Solubility ◽  
Water Soluble ◽  
Voltage Sensitivity ◽  
Chemical Transformations ◽  
Direct Modification ◽  
Biological Compatibility ◽  
Meso Position ◽  
Ionizable Groups ◽  
Boron Center

Fluorophores based on the BODIPY scaffold are prized for their tunable excitation and emission profiles, mild syntheses, and biological compatibility. Improving the water-solubility of BODIPY dyes remains an outstanding challenge. The development of water-soluble BODIPY dyes usually involves direct modification of the BODIPY fluorophore core with ionizable groups or substitution at the boron center. While these strategies are effective for the generation of water-soluble fluorophores, they are challenging to implement when developing BODIPY-based indicators: direct modification of BODIPY core can disrupt the electronics of the dye, complicating the design of functional indicators; and substitution at the boron center often renders the resultant BODIPY incompatible with the chemical transformations required to generate fluorescent sensors. In this study, we show that BODIPYs bearing a sulfonated aromatic group at the meso position provide a general solution for water-soluble BODIPYs. We outline the route to a suite of 5 new sulfonated BODIPYs with 2,6-disubstitution patterns spanning a range of electron-donating and -withdrawing propensities. To highlight the utility of these new, sulfonated BODIPYs, we further functionalize them to access 13 new, BODIPY-based voltage-sensitive fluorophores. The most sensitive of these BODIPY VF dyes displays a 48% ΔF/F per 100 mV in mammalian cells. Two additional BODIPY VFs show good voltage sensitivity (≥24% ΔF/F) and excellent brightness in cells. These compounds can report on action potential dynamics in both mammalian neurons and human stem cell-derived cardiomyocytes. Accessing a range of substituents in the context of a water soluble BODIPY fluorophore provides opportunities to tune the electronic properties of water-soluble BODIPY dyes for functional indicators.

Substitution of hydroxide by fluoride at the boron center of a BODIPY dye

2010 ◽  
Vol 131 (11) ◽  
pp. 1182-1186 ◽  
Author(s):  
Todd W. Hudnall ◽  
Tzu-Pin Lin ◽  
François P. Gabbaï
Keyword(s):  
Boron Center

Synthesis and Properties of 2-(Dimesitylboryl)benzylideneamines

2009 ◽  
Vol 64 (11-12) ◽  
pp. 1381-1386 ◽  
Author(s):  
Zureima García-Hernández ◽  
François P. Gabbaï
Keyword(s):  
Excited State ◽  
Nitrogen Atom ◽  
Intramolecular Charge Transfer ◽  
Quantum Yields ◽  
Structural Studies ◽  
Green Fluorescence ◽  
Imine Nitrogen ◽  
Td Dft ◽  
Imine Nitrogen Atom ◽  
Boron Center

Lithiation of 2-(2-bromophenyl)-dioxolane (1) followed by reaction with dimesitylboron fluoride afforded 2-(2-dimesitylborylphenyl)-dioxolane (2) which was deprotected to afford 2- dimesitylboryl-benzaldehyde (3). Compound 3 reacts with aliphatic amines such as n-butylamine and ethanolamine to afford the corresponding imines 2-(dimesitylboryl)benzylidenebutylamine (4) and 2-(dimesitylboryl)benzylideneethanolamine (5), respectively. Structural studies indicate coordination of the imine-nitrogen atom to the boron center. Imines 4 and 5 emit a green fluorescence near 510 nm with quantum yields approaching 10%. TD-DFT calculations suggest that this emission arises from an intramolecular charge-transfer excited state

Application of the boron center for the design of a covalently bonded closely spaced triad of porphyrin-fullerene mediated by dipyrromethane

2017 ◽  
Vol 46 (19) ◽  
pp. 6278-6290 ◽  
Author(s):  
Di Gao ◽  
Shawkat M. Aly ◽  
Paul-Ludovic Karsenti ◽  
Gessie Brisard ◽  
Pierre D. Harvey
Keyword(s):  
Charge Separation ◽  
Covalently Bonded ◽  
Boron Center

Charge separation stabilization is achieved by placing porphyrin and C60 at the two ends of central BODIPY.

scholarly journals Unique reactivity of B in B[Ge9Y3]3 (Y = H, CH3, BO, CN): formation of a Lewis base

2019 ◽  
Vol 21 (42) ◽  
pp. 23301-23304
Author(s):  
G. Naaresh Reddy ◽  
Rakesh Parida ◽  
R. Inostroza-Rivera ◽  
Arindam Chakraborty ◽  
Puru Jena ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Lewis Base ◽  
Lewis Acidity ◽  
Boron Compounds ◽  
Zintl Ion ◽  
Acid Nature ◽  
Boron Center

Boron compounds usually exhibit Lewis acidity at the boron center due to the presence of vacant p-orbitals. But using Zintl-ion based groups (Ge9Y3, Y = H, CH3, BO, CN), we can alter Lewis acid nature of B to a Lewis base.

Coordination Properties of Organoborate Ligands - Steric Hindrance Around the Distal Boron Center Directs the Conformation of the Dialkylbis(imidazolyl)borate Scaffold

2010 ◽  
Vol 2010 (35) ◽  
pp. 5529-5537 ◽  
Author(s):  
Shiro Hikichi ◽  
Koyu Fujita ◽  
Yoshitaka Manabe ◽  
Munetaka Akita ◽  
Jun Nakazawa ◽  
...  
Keyword(s):  
Steric Hindrance ◽  
Coordination Properties ◽  
Boron Center

Oxidative C(sp3)–H bond cleavage, C–C and CC coupling at a boron center with O2 as the oxidant mediated by platinum(ii)

2014 ◽  
Vol 50 (40) ◽  
pp. 5376-5378 ◽  
Author(s):  
S. Pal ◽  
P. Y. Zavalij ◽  
A. N. Vedernikov
Keyword(s):  
Bond Cleavage ◽  
Boron Center

Platinum(ii) 1,5-cyclooctanediyldi(2-pyridyl)borates react with O2via C(sp3)–H bond cleavage and stepwise C–C and CC coupling of the borate ligand.

Dual function of the boron center of BH(CO)2/BH(N2)2 in halogen- and triel-bonded complexes with hypervalent halogens

2018 ◽  
Vol 84 ◽  
pp. 118-124 ◽  
Author(s):  
Wenbo Dong ◽  
Yanqing Wang ◽  
Xin Yang ◽  
Jianbo Cheng ◽  
Qingzhong Li
Keyword(s):  
Dual Function ◽  
Boron Center ◽  
Bonded Complexes

A snapshot of inorganic Janovsky complex analogues featuring a nucleophilic boron center

2017 ◽  
Vol 53 (95) ◽  
pp. 12734-12737 ◽  
Author(s):  
Di Wu ◽  
Yongxin Li ◽  
Rakesh Ganguly ◽  
Rei Kinjo
Keyword(s):  
Ionic Species ◽  
Boron Center

The addition of phenyl lithium (PhLi) to an aromatic 1,3,2,5-diazadiborinine (1) afforded isolable ionic species 2, which can be deemed as an inorganic analogue of a Janovsky complex.

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