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Volumn 16, Issue 9, 2010, Pages 2887-2903

Dihydronaphthalene-fused boron-dipyrromethene (BODIPY) dyes: Insight into the electronic and conformational tuning modes of BODIPY fluorophores

Author keywords

Boron; Dyes pigments; Fluorescent probes; Photophysics; Protonation

Indexed keywords

A-CARBON; ACIDIC PH; DIBUTYL ETHER; DIPYRROMETHENE; DUAL FLUORESCENCE; DYES/PIGMENTS; ELECTRON-DONATING; ENHANCED FLUORESCENCE; FLUORESCENCE QUANTUM YIELD; FLUORESCENT PROBES; HYDROGEN ATOMS; INTENSE EMISSION; LATEX BEADS; MESO POSITIONS; METHYL GROUP; NEW SERIES; NITROGEN ATOM; PH-RESPONSIVE; PHENYL GROUP; PHOTOPHYSICS; POLAR ENVIRONMENTS; POLAR SOLVENTS; POSITIVELY CHARGED; QUANTUM-CHEMICAL MODELLING; RED SHIFT; RELATED COMPOUNDS; RHODAMINE DYES; SPECTRAL SHIFT; SPECTROSCOPIC PROPERTY; STERIC CROWDING; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

EID: 77149155291     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902527     Document Type: Article
Times cited : (99)

References (94)
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    • Number of hits of articles for the search topic (BODIPY* or borondipyrromethen* or boron-dipyrrin*) and (dye* or fluorophor* or chromophor* or label* or probe* or sensor* or stain* or chemosensor* or indicator*) in ISI Web of Science database as of September 5, 2009: 556 (2005 and later), 264 (2000-2004), 147 (1995-1999) and 28 (1994 and before).
    • Number of hits of articles for the search topic (BODIPY* or borondipyrromethen* or boron-dipyrrin*) and (dye* or fluorophor* or chromophor* or label* or probe* or sensor* or stain* or chemosensor* or indicator*) in ISI Web of Science database as of September 5, 2009: 556 (2005 and later), 264 (2000-2004), 147 (1995-1999) and 28 (1994 and before).
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    • Whereas most cyanines and rhodamines are intrinsically positively charged, for fluoresceins, only the negatively charged dianion form is highly fluorescent. See
    • Whereas most cyanines and rhodamines are intrinsically positively charged, for fluoresceins, only the negatively charged dianion form is highly fluorescent. See, H. Diehl, R. Markuszewski, Talanta 1989, 36, 416-418.
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    • These rules of thumb only pertain to the absorption maxima since only the ground-state dipole moment of all the BODIPY dyes listed in the scheme is sufficiently small so that solvent-polarity-dependent shifts can be neglected. Moreover, for 4 and 5, the 4-iodophenyl substituent in the meso position has virtually no influence on the BODIPY-centred S 1←S0 transition. The same accounts for the meso-hydroxyquinoline groups in 8 and 11 because of their perpendicular orientation. See the original publications for detailed discussions of these compounds
    • 0 transition. The same accounts for the meso-hydroxyquinoline groups in 8 and 11 because of their perpendicular orientation. See the original publications for detailed discussions of these compounds.
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    • Because of these findings and the inherent uncertainties that would accompany a deconvolution of the highly overlapping bands, we refrained from a derivation of global-band or single-transition oscillator strengths from solution absorption spectra
    • Because of these findings and the inherent uncertainties that would accompany a deconvolution of the highly overlapping bands, we refrained from a derivation of global-band or single-transition oscillator strengths from solution absorption spectra.
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    • Derivative spectroscopy is well suited for analysing shoulders and overlapping bands, see, for example, Springer, Berlin
    • Derivative spectroscopy is well suited for analysing shoulders and overlapping bands, see, for example, H.-H. Perkampus, UV-VIS Spectroscopy and Its Applications, Springer, Berlin, 1992, pp. 88-94.
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    • The fluorescence excitation spectra are independent of emission wavelength and basically match the absorption spectra
    • The fluorescence excitation spectra are independent of emission wavelength and basically match the absorption spectra.
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    • f yields an even better agreement. See Table S2 in the Supporting Information.
    • f yields an even better agreement. See Table S2 in the Supporting Information.
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    • VH) in which r=anisotropy, F=fluorescence intensity and subscripts V and H represent vertically and horizontally aligned polarisers.
    • VH) in which r=anisotropy, F=fluorescence intensity and subscripts V and H represent vertically and horizontally aligned polarisers.
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    • The higher transitions (<400 nm) are presumably mixed and involve various molecular orbitals localised asymmetrically on the dihydronaphthalene- BODIPY fragment. Since these transitions are not relevant within the context of this manuscript, no further assignment was attempted.
    • The higher transitions (<400 nm) are presumably mixed and involve various molecular orbitals localised asymmetrically on the dihydronaphthalene- BODIPY fragment. Since these transitions are not relevant within the context of this manuscript, no further assignment was attempted.
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    • Gaussian 03, Revision D.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanaya
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    • To find the best compromise between reasonable processing times and sufficiently accurate modelling for our present purposes, we first performed a theoretical treatment of 1a with the B3LYP functional and different basis sets (6-31G, 6-31G(d, and 6-31G(d,p, and compared key structural parameters thus obtained with experimental results from X-ray analysis (see Table S3 in the Supporting Information for an overview, These trials revealed good agreement of the experimental results with the results obtained for the 6-31G(d) and 6-31G(d,p) basis sets and that the latter do not show significant differences. The 6-31G(d) basis set was thus chosen here
    • To find the best compromise between reasonable processing times and sufficiently accurate modelling for our present purposes, we first performed a theoretical treatment of 1a with the B3LYP functional and different basis sets (6-31G, 6-31G(d), and 6-31G(d,p)) and compared key structural parameters thus obtained with experimental results from X-ray analysis (see Table S3 in the Supporting Information for an overview). These trials revealed good agreement of the experimental results with the results obtained for the 6-31G(d) and 6-31G(d,p) basis sets and that the latter do not show significant differences. The 6-31G(d) basis set was thus chosen here.
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    • pp found here, 29.4 and 29.9° for 1c and 1d, respectively.
    • pp found here, 29.4 and 29.9° for 1c and 1d, respectively.
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    • [30, 35]
    • [30, 35]
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    • 0 transition in the model dyes.
    • 0 transition in the model dyes.
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    • a data obtained by fluorescence agree well with those measured by absorption for all the dyes investigated here (±0.04 units). However, in contrast to the strong increase in fluorescence, protonation is only visible by a shift of the main BODIPY band of about 3 nm (3b) to 13 nm (10b) in absorption.
    • a data obtained by fluorescence agree well with those measured by absorption for all the dyes investigated here (±0.04 units). However, in contrast to the strong increase in fluorescence, protonation is only visible by a shift of the main BODIPY band of about 3 nm (3b) to 13 nm (10b) in absorption.
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    • With an ethylene bridge between N and S/O, through-space and through-bond inductive effects might both play a role
    • With an ethylene bridge between N and S/O, through-space and through-bond inductive effects might both play a role.
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    • + at the considerably low buffer concentrations employed in that study.
    • + at the considerably low buffer concentrations employed in that study.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.