Boron-diindomethene (BDI) dyes and their tetrahydrobicyclo precursors - En route to a new class of highly emissive fluorophores for the red spectral range

Chemistry - A European Journal

Volumn 10, Issue 19, 2004, Pages 4853-4871

  Shen, Zhen ^a,c   Röhr, Holger ^b,d   Rurack, Knut ^b   Uno, Hidemitsu ^a   Spieles, Monika ^b   Schulz, Burkhard ^b   Reck, Günter ^b   Ono, Noboru ^a  

^a EHIME UNIVERSITY   (Japan)

^b BAM FEDERAL INSTITUTE FOR MATERIALS RESEARCH AND TESTING   (Germany)

^c NANJING UNIVERSITY   (China)

^d FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Charge transfer; Dyes pigments; Electron transfer; Fluorescence

Indexed keywords

ABSORPTION; AROMATIC COMPOUNDS; BORON; CHEMICAL MODIFICATION; CHROMOPHORES; ELECTROCHEMISTRY; FUSION REACTIONS; MOLECULAR ORIENTATION; QUENCHING; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL);

BORON-DIINDOMETHENE (BDI); INTRAMOLECULAR QUENCHING; OPTICAL SPECTROSCOPY; TETRAHYROBICICLO PRECURSORS (BC-BDP);

DYES;

BICYCLO COMPOUND; BORON; BORON DIINDOMETHENE; DYE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CHROMATOPHORE; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; ELECTROCHEMICAL ANALYSIS; ELECTRON TRANSPORT; FLUORESCENCE; OXIDATION REDUCTION REACTION; PHOTOCHEMICAL QUENCHING; PRECURSOR; RECEPTOR AFFINITY; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

ACETONITRILES; BORON COMPOUNDS; ELECTROCHEMISTRY; FLUORESCENT DYES; KINETICS; METHANOL; MODELS, MOLECULAR; ORGANIC CHEMICALS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY;

EID: 5544246433     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400173     Document Type: Article

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98. We have already studied some features of these dyes (J L Bricks, J L. Slominskii, M. A. Kudinova, A. I. Tolmachev, K Rurack, U. Resch-Genger, W. Rettig, J. Photochem Photobiol A 2000, 132, 193-208, compounds 8a-c are equivalent to compounds 1a-c in that paper), and they were reinvestigated here only as polymethine model systems. In the fits of the respective spectra of these cyanines 8a-c, performed here for comparison, four species also had to be employed to describe the bands satisfactorily.
99. The BDP (and the bc-BDP) chromophore can be considered as a cross-conjugated polymethine,[23] consisting of a trimethine and a nonamethine chain. On formal consideration, the BDI core constitutes a doubly cross-conjugated polymethine with an additional heptadecamethine chain
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101. -1
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103. LC
104. In accordance with the room-temperature behavior of 3b in acetomtrile, no long wavelength CT emission band could be detected for 3 b in ethanol at 299 K or at any lower temperature.
105. Phosphorescence could not be detected for any of the dyes at 77 K in the wavelength range up to 850 nm and at various delay times in the range of 0.05-100 ms with a Perkin-Elmer LS50B spectrometer with a low-temperature luminescence accessory, flash lamp excitation (fwhm < 10 μs), and gated PMT.
106. -1; see M Maus, W Rettig, J Phys Chem A 2002, 106, 2104-2111)
107. -1; see M Maus, W Rettig, J Phys Chem A 2002, 106, 2104-2111)
108. VH) with r=anisotropy, F=fluorescence intensity and subscripts V and H = vertically and horizontally aligned polarizers Measurements above and below the glass point of ethanol at 170 and 140 K yielded very similar results in the case of 3b
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110. +, respectively
111. Note that these experimental data are well reproduced by the theoretical data given in Section S1 of the Supporting Information.
112. 0 transition involves the HOMO-1/-2 and LUMO with the former MOs being again largely localized on the bicyclo fragments (see Supporting Information) We thus tentatively assign the broad band on the high-energy side which overlaps considerably with the cyanine-type band to this transition and took this into account during spectral analysis
113. The biexponential decay of 4e in MeOH is presumably caused by hydrogen bonding of solvent molecules to the benzocrown donor atoms
114. Note that the electrochemical data listed for 3 f in Table 6 do not show any peculiarities or hint at any such excited-state (quenching) reaction mechanism
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118. + The fluorescence of the latter species, occurring at λ = 830 nm, is narrow and rather resonant. As this behavior is not straightforward and thus cannot be readily exploited for analytical sensing applications, we will not discuss the aggregation phenomena of 4e in detail here.
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