Rational design and synthesis of a novel class of highly fluorescent rhodamine dyes that have strong absorption at long wavelengths
A novel class of strongly fluorescent rhodamine dyes were designed and synthesized by extending the π conjugation of chromophore with limited flexibility. These dyes were shown to have longer absorption in the range of 581 to 631 nm with quantum yields between 0.64 and 0.89. Graphic
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| Published in | Tetrahedron letters Vol. 44; no. 23; pp. 4355 - 4359 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
02.06.2003
Elsevier |
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| Abstract | A novel class of strongly fluorescent rhodamine dyes were designed and synthesized by extending the π conjugation of chromophore with limited flexibility. These dyes were shown to have longer absorption in the range of 581 to 631 nm with quantum yields between 0.64 and 0.89.
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| AbstractList | A novel class of strongly fluorescent rhodamine dyes were designed and synthesized by extending the pi conjugation or chromophore with limited flexibility. These dyes were shown to have longer absorption in the range of 581 to 631 nm with quantum yields between 0.64 and 0.89. (C) 2003 Elsevier Science Ltd. All rights reserved. A novel class of strongly fluorescent rhodamine dyes were designed and synthesized by extending the π conjugation of chromophore with limited flexibility. These dyes were shown to have longer absorption in the range of 581 to 631 nm with quantum yields between 0.64 and 0.89. Graphic |
| Author | Patch, Brian Diwu, Zhenjun Haugland, Richard P. Liu, Jixiang Leung, Wai-Yee Lu, Yixin |
| Author_xml | – sequence: 1 givenname: Jixiang surname: Liu fullname: Liu, Jixiang email: jixiang.liu@probes.com organization: Molecular Probes, Inc., 29851 Willow Creek Road, Eugene, OR 97402, USA – sequence: 2 givenname: Zhenjun surname: Diwu fullname: Diwu, Zhenjun organization: Molecular Devices, Inc., 1311 Orleans Drive, Sunnyvale, CA 94089, USA – sequence: 3 givenname: Wai-Yee surname: Leung fullname: Leung, Wai-Yee organization: Molecular Probes, Inc., 29851 Willow Creek Road, Eugene, OR 97402, USA – sequence: 4 givenname: Yixin surname: Lu fullname: Lu, Yixin organization: Molecular Probes, Inc., 29851 Willow Creek Road, Eugene, OR 97402, USA – sequence: 5 givenname: Brian surname: Patch fullname: Patch, Brian organization: Molecular Probes, Inc., 29851 Willow Creek Road, Eugene, OR 97402, USA – sequence: 6 givenname: Richard P. surname: Haugland fullname: Haugland, Richard P. organization: Molecular Probes, Inc., 29851 Willow Creek Road, Eugene, OR 97402, USA |
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| References | 8.22 (d, 1H; aromatic H), 7.78 (t, 1H; aromatic H), 7.72 (t, 1H; aromatic H), 7.39 (d, 2H; heteroaromatic H), 7.34 (d, 1H; aromatic H), 7.31 (s, 2H; aromatic H), 7.06 (d, 2H; heteroaromatic H), 6.93 (s, 2H; aromatic H), 3.12 (s, 6H; CH Sauer, Han, Muller, Nord, Schulz, Seeger, Wolfrum, Arden-Jacob, Deltau, Marx, Zander, Drexhage (BIB3) 1995; 5 Badone, Baroni, Cardamone, Ielmini, Guzzi (BIB7) 1997; 62 DMSO 0.26 CHCl H NMR (400 MHz, CDCl MeOH (v/v 10:1), yield 68%; mp 118–120°C (%): 818 (100) (%) 834 (100) MeOH (v/v 10:1), yield 18%; mp 250°C (dec.) 7.10 (d, 2H; heteroaromatic H), 6.85 (d, 2H; heteroaromatic H), 6.65 (s, 2H; aromatic H), 6.40 (s, 2H; aromatic H), 2.97 (s, 6H; CH 1.73 (s, 6H; CH 0.22 CHCl 8.93 (s, 5-isomer; aromatic H), 8.37 (m, 5- and 6-isomer; aromatic H), 8.32 (d; 6-isomer; aromatic H), 8.00 (s, 6-isomer; aromatic H), 7.39 (m, 2H; heteroaromatic H), 7.08 (m, 2H; heteroaromatic H), 6.99 (m, 4H; aromatic H), 3.29, 3.28 (2×s, 6H; CH ) 1.76, 1.75, 1.74 (3×s, 12H; CH MeOH (v/v 5:1), yield 61%; mp >300°C , 1.56 (s, 6H; CH . MS (EI) / 2.00 (s, 12H; CH MeOH (v/v 10:1), yield 26%; mp 240°C (dec.) (%) 645 (100) 8.34 (s, 1H; aromatic H), 7.79 (d, 1H; aromatic H), 7.52 (d, 2H; heteroaromatic H), 7.24 (m, 3H; aromatic and heteroaromatic H), 6.94 (s, 2H; aromatic H), 6.82 (s, 2H; aromatic H), 3.25 (s, 6H; CH MeOH (%): 591 (100) 1.60 (s, 12H; CH 352–358. H]. MeOH (v/v 10:1), yield 30%; mp 275°C (dec.) 0.14/0.34 CHCl 8.24 (d, H; aromatic H), 7.80 (t, 1H; aromatic H), 7.32 (t, 1H; aromatic H), 7.65 (s, 2H; aromatic H), 7.50 (d, 2H; aromatic H), 7.45 (d, 2H; aromatic H), 7.35 (m, 3H; aromatic H), 7.28 (t, 2H; aromatic H), 6.94 (s, 2H; aromatic H), 3.10 (s, 6H; CH purple–blue solid blue solid 0.09 CHCl For bioconjugates and applications, see: Diwu, Z.; Liu, J.; Haugland, R. P.; Gee, K. R. PCT Int. Appl. WO 02 12,195, 2002. 0.29 CHCl 2.00, 1.99, 1.96, 1.90 (4×s, 12H; CH (%) 740 (100) 2.00 (s, 6H; CH Forster (BIB6) 1951 1.72 (s, 6H; CH MeOH (v/v 5:1), yield 67%; mp >300°C MeOH (v/v 10:1), yield 70%; mp 177–180°C (%): 603 (100) Haugland (BIB2) 2002 MeOH (v/v 5:1), yield 88%; mp >300°C and 8.90 (s, 5-isomer; aromatic H), 8.38 (d, 6-isomer, aromatic H), 8.28 (m, 5- and 6-isomer; aromatic H), 8.09 (s, 6-isomer; aromatic H), 7.93 (d, 5-isomer; aromatic H), 7.89 (d, 2H; aromatic H), 7.78 (d, 2H; aromatic H), 7.34 (m, 4H; aromatic H), 7.07, 7.04 (2×s, 2H; aromatic H), 6.90, 6.85 (2×s, 2H; aromatic H), 3.37, 3.27 (2×s, 6H; CH MeOH (v/v 5:1), yield 85%; mp >300°C H NMR (400 MHz Arden, J.; Deltau, G.; Huth, V.; Kringel, U.; Peros, D.; Drexhage, K. H. Herrmann, R.; Josel, H. P.; Drexhage, K. H.; Arden-Jacob, J. US Patent 5,750,409, 1998. 0.14/0.41 CHCl 1.60 (s, 6H; CH 7.10 (d, 2H; heteroaromatic H), 6.85 (d, 2H; heteroaromatic H), 6.70 (s, 2H; aromatic H), 6.45 (s, 2H; aromatic H), 2.98 (s, 6H; CH 1.70 (s, 6H; CH 8.37 (s, 1H; aromatic H), 8.03 (m, 4H; aromatic H), 7.83 (d, 1H; aromatic H), 7.38 (m, 4H; aromatic H), 7.28 (d, 1H; aromatic H), 6.94 (s, 2H; aromatic H), 6.89 (s, 2H; aromatic), 3.27 (s, 6H; CH Drexhage (BIB1) 1973; 1 (%) 745 (100) 1.69 (s, 3H; CH (%): 719 (100) 0.21 CHCl (%) 675 (100) 0.10 CHCl 1.98 (s, 6H; CH Benson, S. C.; Lam, J. Y. L.; Menchen, S. M. US Patent 5,936,087, 1999. 8.14 (d, 2H; aromatic H), 7.72 (d, 2H; aromatic H), 7.65 (d, 2H; aromatic H), 7.52 (m, 2H; aromatic H), 7.40 (m, 4H; aromatic H), 7.01 (s, 2H; aromatic H), 6.41 (s, 2H; aromatic H), 3.02 (s, 6H; CH (WOS:000183118400012.3) 1999 FORSTER T (WOS:000183118400012.8) 1951 (WOS:000183118400012.1) 2002 Badone, D (WOS:A1997YC65700026) 1997; 62 (WOS:000183118400012.2) 1998 ARDEN, J (WOS:A1991FC34400072) 1991; 48-9 DREXHAGE KH (WOS:000183118400012.7) 1973; 1 Sauer, M (MEDLINE:24226792) 1995; 5 HAUGLAND RP (WOS:000183118400012.9) 2002 Badone (10.1016/S0040-4039(03)00938-9_BIB7) 1997; 62 10.1016/S0040-4039(03)00938-9_BIB10 10.1016/S0040-4039(03)00938-9_BIB5 Haugland (10.1016/S0040-4039(03)00938-9_BIB2) 2002 10.1016/S0040-4039(03)00938-9_BIB4 Forster (10.1016/S0040-4039(03)00938-9_BIB6) 1951 10.1016/S0040-4039(03)00938-9_BIB9 10.1016/S0040-4039(03)00938-9_BIB8 Drexhage (10.1016/S0040-4039(03)00938-9_BIB1) 1973; 1 Sauer (10.1016/S0040-4039(03)00938-9_BIB3) 1995; 5 |
| References_xml | – year: 1951 ident: BIB6 publication-title: Fluoreszenz Organischer Verbindungen contributor: fullname: Forster – volume: 1 start-page: 144 year: 1973 end-page: 274 ident: BIB1 publication-title: Top. Appl. Phys. contributor: fullname: Drexhage – volume: 5 start-page: 247 year: 1995 end-page: 261 ident: BIB3 publication-title: J. Fluoresc. contributor: fullname: Drexhage – year: 2002 ident: BIB2 publication-title: Handbook of Fluorescent Probes and Research Products contributor: fullname: Haugland – volume: 62 start-page: 7170 year: 1997 end-page: 7173 ident: BIB7 publication-title: J. Org. Chem. contributor: fullname: Guzzi – year: 1998 ident: WOS:000183118400012.2 – volume: 48-9 start-page: 352 year: 1991 ident: WOS:A1991FC34400072 article-title: FLUORESCENCE AND LASING PROPERTIES OF RHODAMINE DYES publication-title: JOURNAL OF LUMINESCENCE contributor: fullname: ARDEN, J – year: 2002 ident: WOS:000183118400012.1 – year: 2002 ident: WOS:000183118400012.9 publication-title: HDB FLUORESCENT PROB contributor: fullname: HAUGLAND RP – year: 1951 ident: WOS:000183118400012.8 publication-title: FLUORESZENZ ORG VERB contributor: fullname: FORSTER T – volume: 62 start-page: 7170 year: 1997 ident: WOS:A1997YC65700026 article-title: Highly efficient palladium-catalyzed boronic acid coupling reactions in water: Scope and limitations publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Badone, D – year: 1999 ident: WOS:000183118400012.3 – volume: 1 start-page: 144 year: 1973 ident: WOS:000183118400012.7 publication-title: TOP APPL PHYS contributor: fullname: DREXHAGE KH – volume: 5 start-page: 247 year: 1995 ident: MEDLINE:24226792 article-title: New fluorescent dyes in the red region for biodiagnostics. publication-title: Journal of fluorescence doi: 10.1007/BF00723896 contributor: fullname: Sauer, M – ident: 10.1016/S0040-4039(03)00938-9_BIB5 – volume: 62 start-page: 7170 year: 1997 ident: 10.1016/S0040-4039(03)00938-9_BIB7 publication-title: J. Org. Chem. doi: 10.1021/jo970439i contributor: fullname: Badone – volume: 5 start-page: 247 year: 1995 ident: 10.1016/S0040-4039(03)00938-9_BIB3 publication-title: J. Fluoresc. doi: 10.1007/BF00723896 contributor: fullname: Sauer – year: 1951 ident: 10.1016/S0040-4039(03)00938-9_BIB6 contributor: fullname: Forster – volume: 1 start-page: 144 year: 1973 ident: 10.1016/S0040-4039(03)00938-9_BIB1 publication-title: Top. Appl. Phys. doi: 10.1007/978-3-662-11579-4_4 contributor: fullname: Drexhage – ident: 10.1016/S0040-4039(03)00938-9_BIB8 – ident: 10.1016/S0040-4039(03)00938-9_BIB4 – ident: 10.1016/S0040-4039(03)00938-9_BIB9 – year: 2002 ident: 10.1016/S0040-4039(03)00938-9_BIB2 contributor: fullname: Haugland – ident: 10.1016/S0040-4039(03)00938-9_BIB10 |
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| Snippet | A novel class of strongly fluorescent rhodamine dyes were designed and synthesized by extending the π conjugation of chromophore with limited flexibility.... A novel class of strongly fluorescent rhodamine dyes were designed and synthesized by extending the pi conjugation or chromophore with limited flexibility.... |
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| Title | Rational design and synthesis of a novel class of highly fluorescent rhodamine dyes that have strong absorption at long wavelengths |
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