- -

Structure and Conformational Studies of Aza-Crown 8-Amino-BODIPY Derivatives: Influence of Steric Hindrance on Their Photophysical Properties

RiuNet: Institutional repository of the Polithecnic University of Valencia

Share/Send to

Cited by

Statistics

Structure and Conformational Studies of Aza-Crown 8-Amino-BODIPY Derivatives: Influence of Steric Hindrance on Their Photophysical Properties

Show full item record

Costero, AM.; Betancourt-Mendiola, M.; Gaviña, P.; Ochando Gómez, LE.; Gil Grau, S.; Chulvi, K.; Peña-Cabrera, E. (2017). Structure and Conformational Studies of Aza-Crown 8-Amino-BODIPY Derivatives: Influence of Steric Hindrance on Their Photophysical Properties. European Journal of Organic Chemistry. 42:6283-6290. https://doi.org/10.1002/ejoc.201701016

Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/140194

Files in this item

Item Metadata

Title: Structure and Conformational Studies of Aza-Crown 8-Amino-BODIPY Derivatives: Influence of Steric Hindrance on Their Photophysical Properties
Author: Costero, Ana M. Betancourt-Mendiola, M.L. Gaviña, Pablo Ochando Gómez, Luis Enrique Gil Grau, Salvador Chulvi, Katherine Peña-Cabrera, E.
UPV Unit: Universitat Politècnica de València. Instituto de Reconocimiento Molecular y Desarrollo Tecnológico - Institut de Reconeixement Molecular i Desenvolupament Tecnològic
Issued date:
Abstract:
[EN] Herein, we report the synthesis, X-ray crystal structure and photophysical studies of six new 8-amino-BODIPY derivatives containing crown or azo-crown ether moieties. The influence of steric hindrance, caused by the ...[+]
Subjects: Functional organic materials , Dyes , Pigments , Crown compounds , Fluorescence , Solid-state structures , Zinc
Copyrigths: Cerrado
Source:
European Journal of Organic Chemistry. (issn: 1434-193X )
DOI: 10.1002/ejoc.201701016
Publisher:
John Wiley & Sons
Publisher version: https://doi.org/10.1002/ejoc.201701016
Project ID:
MINISTERIO DE ECONOMIA Y COMPETITIVIDAD/MAT2015-64139-C4-4-R
GV/PROMETEOII/2014/047
CONACYT/123732
CONACYT/253623
Thanks:
We thank the Spanish Government, Fondos Europeos para el Desarrollo Regional (FEDER) (MAT2015-64139-C4-4-R) and the Generalitat Valenciana (PROMETEOII/2014/047) for support. SCSIE (Universitat de Valencia) is gratefully ...[+]
Type: Artículo

References

Boens, N., Leen, V., & Dehaen, W. (2012). Fluorescent indicators based on BODIPY. Chem. Soc. Rev., 41(3), 1130-1172. doi:10.1039/c1cs15132k

Loudet, A., & Burgess, K. (2007). BODIPY Dyes and Their Derivatives:  Syntheses and Spectroscopic Properties. Chemical Reviews, 107(11), 4891-4932. doi:10.1021/cr078381n

Ulrich, G., Ziessel, R., & Harriman, A. (2008). The Chemistry of Fluorescent Bodipy Dyes: Versatility Unsurpassed. Angewandte Chemie International Edition, 47(7), 1184-1201. doi:10.1002/anie.200702070 [+]
Boens, N., Leen, V., & Dehaen, W. (2012). Fluorescent indicators based on BODIPY. Chem. Soc. Rev., 41(3), 1130-1172. doi:10.1039/c1cs15132k

Loudet, A., & Burgess, K. (2007). BODIPY Dyes and Their Derivatives:  Syntheses and Spectroscopic Properties. Chemical Reviews, 107(11), 4891-4932. doi:10.1021/cr078381n

Ulrich, G., Ziessel, R., & Harriman, A. (2008). The Chemistry of Fluorescent Bodipy Dyes: Versatility Unsurpassed. Angewandte Chemie International Edition, 47(7), 1184-1201. doi:10.1002/anie.200702070

Ulrich, G., Ziessel, R., & Harriman, A. (2008). Die vielseitige Chemie von Bodipy-Fluoreszenzfarbstoffen. Angewandte Chemie, 120(7), 1202-1219. doi:10.1002/ange.200702070

Kowada, T., Maeda, H., & Kikuchi, K. (2015). BODIPY-based probes for the fluorescence imaging of biomolecules in living cells. Chemical Society Reviews, 44(14), 4953-4972. doi:10.1039/c5cs00030k

Merino, E. J., & Weeks, K. M. (2005). Facile Conversion of Aptamers into Sensors Using a 2‘-Ribose-Linked Fluorophore. Journal of the American Chemical Society, 127(37), 12766-12767. doi:10.1021/ja053189t

Pretzer, E., & Wiktorowicz, J. E. (2008). Saturation fluorescence labeling of proteins for proteomic analyses. Analytical Biochemistry, 374(2), 250-262. doi:10.1016/j.ab.2007.12.014

Rurack, K., Kollmannsberger, M., & Daub, J. (2001). Molecular Switching in the Near Infrared (NIR) with a Functionalized Boron-Dipyrromethene Dye. Angewandte Chemie International Edition, 40(2), 385-387. doi:10.1002/1521-3773(20010119)40:2<385::aid-anie385>3.0.co;2-f

Rurack, K., Kollmannsberger, M., & Daub, J. (2001). Molekulares Schalten im nahen Infrarot (NIR) mit einem funktionalisierten Bordipyrromethen-Farbstoff. Angewandte Chemie, 113(2), 396-399. doi:10.1002/1521-3757(20010119)113:2<396::aid-ange396>3.0.co;2-w

Trieflinger, C., Rurack, K., & Daub, J. (2005). ?Turn ON/OFF your LOV light?: Borondipyrromethene-Flavin Dyads as Biomimetic Switches Derived from the LOV Domain. Angewandte Chemie International Edition, 44(15), 2288-2291. doi:10.1002/anie.200462377

Trieflinger, C., Rurack, K., & Daub, J. (2005). ?Turn ON/OFF your LOV light?: Bordipyrromethen-Flavin-Dyaden als biomimetische, von der LOV-Dom�ne abgeleitete Schalter. Angewandte Chemie, 117(15), 2328-2331. doi:10.1002/ange.200462377

Sunahara, H., Urano, Y., Kojima, H., & Nagano, T. (2007). Design and Synthesis of a Library of BODIPY-Based Environmental Polarity Sensors Utilizing Photoinduced Electron-Transfer-Controlled Fluorescence ON/OFF Switching. Journal of the American Chemical Society, 129(17), 5597-5604. doi:10.1021/ja068551y

Bandichhor, R., Petrescu, A. D., Vespa, A., Kier, A. B., Schroeder, F., & Burgess, K. (2006). Water-Soluble Through-Bond Energy Transfer Cassettes for Intracellular Imaging. Journal of the American Chemical Society, 128(33), 10688-10689. doi:10.1021/ja063784a

Gotor, R., Costero, A. M., Gil, S., Parra, M., Martínez-Máñez, R., Sancenón, F., & Gaviña, P. (2013). Selective and sensitive chromogenic detection of cyanide and HCN in solution and in gas phase. Chemical Communications, 49(50), 5669. doi:10.1039/c3cc80006g

Barba-Bon, A., Costero, A. M., Gil, S., Harriman, A., & Sancenón, F. (2014). Highly Selective Detection of Nerve-Agent Simulants with BODIPY Dyes. Chemistry - A European Journal, 20(21), 6339-6347. doi:10.1002/chem.201304475

Chapran, M., Angioni, E., Findlay, N. J., Breig, B., Cherpak, V., Stakhira, P., … Skabara, P. J. (2017). An Ambipolar BODIPY Derivative for a White Exciplex OLED and Cholesteric Liquid Crystal Laser toward Multifunctional Devices. ACS Applied Materials & Interfaces, 9(5), 4750-4757. doi:10.1021/acsami.6b13689

Esnal, I., Duran-Sampedro, G., Agarrabeitia, A. R., Bañuelos, J., García-Moreno, I., Macías, M. A., … Ortiz, M. J. (2015). Coumarin–BODIPY hybrids by heteroatom linkage: versatile, tunable and photostable dye lasers for UV irradiation. Physical Chemistry Chemical Physics, 17(12), 8239-8247. doi:10.1039/c5cp00193e

Roacho, R. I., Metta-Magaña, A., Portillo, M. M., Peña-Cabrera, E., & Pannell, K. H. (2013). 8-Amino-BODIPYs: Structural Variation, Solvent-Dependent Emission, and VT NMR Spectroscopic Properties of 8-R2N-BODIPY. The Journal of Organic Chemistry, 78(9), 4245-4250. doi:10.1021/jo302758a

Boens, N., Wang, L., Leen, V., Yuan, P., Verbelen, B., Dehaen, W., … Alvarez-Pez, J. M. (2014). 8-HaloBODIPYs and Their 8-(C, N, O, S) Substituted Analogues: Solvent Dependent UV–Vis Spectroscopy, Variable Temperature NMR, Crystal Structure Determination, and Quantum Chemical Calculations. The Journal of Physical Chemistry A, 118(9), 1576-1594. doi:10.1021/jp412132y

Osorio-Martínez, C. A., Urías-Benavides, A., Gómez-Durán, C. F. A., Bañuelos, J., Esnal, I., López Arbeloa, I., & Peña-Cabrera, E. (2012). 8-AminoBODIPYs: Cyanines or Hemicyanines? The Effect of the Coplanarity of the Amino Group on Their Optical Properties. The Journal of Organic Chemistry, 77(12), 5434-5438. doi:10.1021/jo300724m

De Lourdes Betancourt-Mendiola, M., Peña-Cabrera, E., Gil, S., Chulvi, K., Ochando, L. E., & Costero, A. M. (2014). Concentration depending fluorescence of 8-(di-(2-picolyl))aminoBODIPY in solution. Tetrahedron, 70(23), 3735-3739. doi:10.1016/j.tet.2014.03.095

Müller, B. J., Borisov, S. M., & Klimant, I. (2016). Red- to NIR-Emitting, BODIPY-Based, K+-Selective Fluoroionophores and Sensing Materials. Advanced Functional Materials, 26(42), 7697-7707. doi:10.1002/adfm.201603822

Qin, W., Baruah, M., Sliwa, M., Van der Auweraer, M., De Borggraeve, W. M., Beljonne, D., … Boens, N. (2008). Ratiometric, Fluorescent BODIPY Dye with Aza Crown Ether Functionality: Synthesis, Solvatochromism, and Metal Ion Complex Formation. The Journal of Physical Chemistry A, 112(27), 6104-6114. doi:10.1021/jp800261v

Yang, L., Liao, D.-J., Wu, A., & Yan, H. (2017). Synthesis and fluorescent properties of aza-crown ether tethered BODIPY fluorophores. Tetrahedron Letters, 58(9), 889-891. doi:10.1016/j.tetlet.2017.01.058

Goud, T. V., Tutar, A., & Biellmann, J.-F. (2006). Synthesis of 8-heteroatom-substituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene dyes (BODIPY). Tetrahedron, 62(21), 5084-5091. doi:10.1016/j.tet.2006.03.036

Bañuelos, J., Martín, V., Gómez‐Durán, C. F. A., Córdoba, I. J. A., Peña‐Cabrera, E., García‐Moreno, I., … Arbeloa, Í. L. (2011). New 8‐Amino‐BODIPY Derivatives: Surpassing Laser Dyes at Blue‐Edge Wavelengths. Chemistry – A European Journal, 17(26), 7261-7270. doi:10.1002/chem.201003689

Esnal, I., Urías-Benavides, A., Gómez-Durán, C. F. A., Osorio-Martínez, C. A., García-Moreno, I., Costela, A., … Peña-Cabrera, E. (2013). Reaction of Amines with 8-MethylthioBODIPY: Dramatic Optical and Laser Response to Amine Substitution. Chemistry - An Asian Journal, 8(11), 2691-2700. doi:10.1002/asia.201300760

Kimura, E., Aoki, S., Koike, T., & Shiro, M. (1997). A Tris(ZnII−1,4,7,10-tetraazacyclododecane) Complex as a New Receptor for Phosphate Dianions in Aqueous Solution. Journal of the American Chemical Society, 119(13), 3068-3076. doi:10.1021/ja9640408

Skwierawska, A. M., & Paluszkiewicz, E. (2006). High Yield Synthesis and Preliminary Spectroscopic Study of Mono-N-alkylated Cyclen Derivatives of Salicylic Acid. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 56(3-4), 323-330. doi:10.1007/s10847-006-9101-6

2013 Versions 1.171.36.28 and 1.171.36.21 2013/2012

Sheldrick, G. M. (2015). Crystal structure refinement withSHELXL. Acta Crystallographica Section C Structural Chemistry, 71(1), 3-8. doi:10.1107/s2053229614024218

Farrugia, L. J. (2012). WinGXandORTEP for Windows: an update. Journal of Applied Crystallography, 45(4), 849-854. doi:10.1107/s0021889812029111

2016

Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., … Wood, P. A. (2008). Mercury CSD 2.0– new features for the visualization and investigation of crystal structures. Journal of Applied Crystallography, 41(2), 466-470. doi:10.1107/s0021889807067908

Farrugia, L. J. (1997). ORTEP-3 for Windows - a version ofORTEP-III with a Graphical User Interface (GUI). Journal of Applied Crystallography, 30(5), 565-565. doi:10.1107/s0021889897003117

[-]

This item appears in the following Collection(s)

Show full item record