Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom
Publication type: Journal Article
Publication date: 2019-08-20
scimago Q1
wos Q1
SJR: 0.958
CiteScore: 7.4
Impact factor: 4.7
ISSN: 00201669, 1520510X
PubMed ID:
31430148
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
An efficient synthesis of boron-functionalized cyclic BODIPY-Gly conjugates, using commercially available N-protected glycine amino acids and a BF2-BODIPY moiety as starting materials, is reported. The existence of two conformers (up and down) is revealed through comprehensive DFT calculations and 1H and 11B NMR analyses. The experimental and computational results indicate that all BODIPYs are stable in aqueous solutions at neutral pH and that Fmoc-BODIPY (4) is more stable than Ac-BODIPY (6) in the presence of trifluoroacetic acid (TFA). In part due to their enhanced rigidity, all BODIPY-Gly conjugates display increased fluorescence quantum yields (0.6 < Φ < 0.9) relative to the corresponding BF2-BODIPY, making them excellent candidates for fluorescence imaging applications.
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Total citations:
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Citations from 2024:
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(20.84%)
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GOST
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Wang M. et al. Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom // Inorganic Chemistry. 2019. Vol. 58. No. 17. pp. 11614-11621.
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Wang M., Zhang G., Bobadova-Parvanova P., Merriweather A. N., Odom L., Barbosa D., Fronczek F., Smith K. S., Vicente M. A. Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom // Inorganic Chemistry. 2019. Vol. 58. No. 17. pp. 11614-11621.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.inorgchem.9b01474
UR - https://doi.org/10.1021/acs.inorgchem.9b01474
TI - Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom
T2 - Inorganic Chemistry
AU - Wang, Maodie
AU - Zhang, Guanyu
AU - Bobadova-Parvanova, P.
AU - Merriweather, Ashley N
AU - Odom, Lilian
AU - Barbosa, David
AU - Fronczek, Frank
AU - Smith, Kevin S.
AU - Vicente, M. A.
PY - 2019
DA - 2019/08/20
PB - American Chemical Society (ACS)
SP - 11614-11621
IS - 17
VL - 58
PMID - 31430148
SN - 0020-1669
SN - 1520-510X
ER -
Cite this
BibTex (up to 50 authors)
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@article{2019_Wang,
author = {Maodie Wang and Guanyu Zhang and P. Bobadova-Parvanova and Ashley N Merriweather and Lilian Odom and David Barbosa and Frank Fronczek and Kevin S. Smith and M. A. Vicente},
title = {Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom},
journal = {Inorganic Chemistry},
year = {2019},
volume = {58},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.inorgchem.9b01474},
number = {17},
pages = {11614--11621},
doi = {10.1021/acs.inorgchem.9b01474}
}
Cite this
MLA
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Wang, Maodie, et al. “Synthesis and Investigation of Linker-Free BODIPY–Gly Conjugates Substituted at the Boron Atom.” Inorganic Chemistry, vol. 58, no. 17, Aug. 2019, pp. 11614-11621. https://doi.org/10.1021/acs.inorgchem.9b01474.