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Chemical Structure| 201802-67-7 Chemical Structure| 201802-67-7
Chemical Structure| 201802-67-7
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Rajapaksha, Ishanka N. ; Wang, Jing ; Leszczynski, Jerzy ; Scott, Colleen N. ;

Abstract: NIR dyes have become popular for many applications, including biosensing and imaging. For this reason, the mol. switch mechanism of the xanthene dyes makes them useful for in vivo detection and imaging of bioanalytes. Our group has been designing NIR xanthene-based dyes by the donor-acceptor-donor approach; however, the equilibrium between their opened and closed forms varies depending on the donors and spacer. We synthesized donor-acceptor-donor NIR xanthene-based dyes with an alkyne spacer via the Sonogashira coupling reaction to investigate the effects of the alkyne spacer and the donors on the maximum absorption wavelength and the mol. switching (ring opening) process of the dyes. We evaluated the strength and nature of the donors and the presence and absence of the alkyne spacer on the properties of the dyes. It was shown that the alkyne spacer extended the conjugation of the dyes, leading to absorption wavelengths of longer values compared with the dyes without the alkyne group. In addition, strong charge transfer donors shifted the absorption wavelength towards the NIR region, while donors with strong π-donation resulted in xanthene dyes with a smaller equilibrium constant DFT/TDDFT calculations corroborated the exptl. data in most of the cases. Dye 2 containing the N,N-dimethylaniline group gave contrary results and is being further investigated.

Keywords: donor-acceptor-donor ; NIR dyes ; xanthene dyes ; amine donors ; alkyne spacers

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Product Details of 4-(Diphenylamino)benzeneboronic acid

CAS No. :201802-67-7
Formula : C18H16BNO2
M.W : 289.14
SMILES Code : OB(O)C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1
MDL No. :MFCD06798117
InChI Key :TWWQCBRELPOMER-UHFFFAOYSA-N
Pubchem ID :12166934

Safety of 4-(Diphenylamino)benzeneboronic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335-H413
Precautionary Statements:P261-P273-P305+P351+P338
 

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