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Design and Applications of Luminescent Sensing Systems

Design and Applications of Luminescent Sensing Systems. The Miniature James Bond. The PET design generalized in Colombo/Belfast. PET. OFF state. Chem. Rev . 1997, 97 , 1515. Org. Biomol. Chem. 2008, 6 , 2468. Analyst 2009, 134 , 2385. Fluorophore.

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Design and Applications of Luminescent Sensing Systems

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  1. Design and Applications of Luminescent Sensing Systems

  2. The Miniature James Bond

  3. The PET design generalized in Colombo/Belfast PET OFF state Chem. Rev. 1997, 97, 1515 Org. Biomol. Chem. 2008, 6, 2468 Analyst 2009, 134, 2385 Fluorophore Spacer Receptor h PET ON state Spacer Receptor Fluorophore M+ h h

  4. Constant Fluorescence Fluorophore < 1 nm Ion-Switchable Fluorescence Fluorophore Spacer Receptor Fluorophore Spacer Receptor M+ > 1 nm

  5. Chatterjee, Kimura, Grigg, Moore, Brown, James, Davidson, Beer, Stoddart, Parker, Williams, Ward, Sutherland Osa, Sakamoto, Walt, Miller, Nakatsuji, Fukuzumi, de Silva, Lippard Shizuka, Teramae, Rettig, Resch, Wolfbeis, Daub, Plater, Yagi, Iwai, Hamachi Leigh, Moller, Rurack, Schuster, Greiner Tanaka, Nagano, Czarnik, Pearson Callan de Silva, Imai, Nagamura, Verhoeven, McCoy Kuhn, Jager Akasaka Gunnlaugsson, Chang, Gee Qian, Valeur, Lehn, Wang, Ma, Yoon, Koide O’Shea, Kruger Peng Shinkai, Kubo, Hamachi Kim Weiss, Leray Wu, Li, Chen, Chang Soumillion Yang Reymond Jiang Leiner Bruckner Smith Pardo Jin Qian, Tian, Morawetz, Turro, Zinic Stoddart, Pina, Pischel, Chen, Hou Lawrence, Adams, Tang, Li Imperiali, Akkaya, Kumar Kulatilleke Marcus, Hsu, Chiu Valkan Tsien, Lodeiro Cary Masilamani Das Barbas, Guo, Lin Lakowicz, Pu Rebek Fabbrizzi, Quici, Diaz-Fernandez Bharadwaj, Khan Gawley, Leblanc Balzani, Prodi, Barigelletti, Lippolis Samanta Whitten Wang, Lindsey Garcia- Espana, Costero, Miranda, Escriche, Luis Bhattacharya, Bianchi, Pallavicini Inoue Maitra D’Souza Tusa, Fahrni, Perry Chattopadyay Brown Ji Selinger Shanzer, de Silva Lincoln Eichen, Willner Rajasekharan, Ajayaghosh, Ramaiah, Varma Bouas-Laurent, Desvergne, Lapouyade, Fages, McClenaghan

  6. Hall, Watkinson, Spring Holdt, Plenio, Moro, Nakamura Sauer, Schalley, Nau, Nielsen, Kilsa Seeberger, Ihmels, Langhals Suzuki Seeberger Cho, Callan Sango Burdette, Kim, Hong Fedorova VanVoorhis Kotschy, Kele McCarroll, Xu, Bojinov, Yunus, Harima, Wang, Zhao Grabchev Hofkens Dyer, Toyooka, Levine Meallet, Ooyama, Magri Wang, Lu Mallet, Yao, Yoshida, Demas Fu Vicens, Saleh Sasamoto Perez- Hancock Tan-Chang Chuburu Guchait, Inestrosa, Zhu, Wang, Ghosh Pischel Sung Zuo, Guo, Lodeiro Mashraqui Huang, Liu, Lei, Jiang He, Ji You Fusi, Heagy, Micheloni, Wang Campagna, Han Flamigni Piccionello Theodorakopoulos Rudkevich, Houston Anslyn De Costa Todd Wainwright Pfeffer Ramamurthy Kruger

  7. Fluorescent PET pH Sensors N Et 2 N O N N Et 2 N H DAYA RUPASINGHE N Et 2 J. Chem. Soc. Chem. Commun. 1985, 1669 NIMAL GUNARATNE LysoSensorTM Blue and Green (Invitrogen)

  8. pH 5.57.78.08.38.58.89.19.5 Fluorescence Intensity 10.5 480 500 420 460 400 440 Wavelength (nm)

  9. 18mm Cancer cells respond to radiation by developing acidic vesicular organelles. Sensor: Lysosensor Blue Paglin et al (Sloan-Kettering Center, NY) Cancer Res. 2001, 61, 439

  10. ‘Off-On’ sensors selective for Na+and K+ Jim Tusa, Marc Leiner Hua-Rui He, Mark Mortellaro (Roche) J. Mater. Chem. 2005, 15, 2640

  11. Potassium Sodium O O O O N N receptor O O O O O O N N O O O spacer N N H H fluorophore O O N N O O linker hydrophilic polymer hydrophilic polymer hydrophilic polymer hydrophilic polymer O O

  12. CO2 O2 pH tHb 100M USD Cassette sales ambulances, hospitals, GP and vet surgeries Na+ K+ Ca++ or Cl- Disposable Cassette and OPTI Critical Care Analyzer (CCA)

  13. Robots for Mapping Small Nanospaces Seiichi Uchiyama (University of Tokyo) Kaoru Iwai (Nara Women’s University) Angew. Chem. Int. Ed. 2008, 47, 4667

  14. A Popular Robot

  15. A Useful Robot Mars Rover ‘Opportunity’ January 2005 ‘Curiosity’ August 2012

  16. receptor receptor ICT fluorophore fluorophore fine positioner gross positioner spacer spacer + H H O N O O N S N N N H O H O 10

  17. pH IF 0 450 500 550 600 650 700 750 800 Wavelength (nm)

  18. 0 0 80 10 40 60 20 30 50 70 – – 0.4 0.4 – – 0.8 p Δ K a – – 1.2 O H O 10 – – 1.6 0 50 60 10 20 20 30 40 40 80 70 O H – – 0.4 O O H p p p K Δ a – – 0.8 O O H Polarity ( Polarity ( ) ) ε ε – – 1.2 1.2 O H

  19. Emulating One-way Electron Traffic of Photosynthesis Jialong Liu Inorg. Chim. Acta 2012, 381, 243

  20. inside membrane outside www.nyu.edu/pages/mathmol/modules/photosynthesis/photo.html

  21. receptor receptor receptor’ receptor ICT fluorophore fluorophore spacer’ spacer spacer spacer d+ d- O O O N N M e N N d- 2 d- O O O N N N M e N 2 d+ H H d+ O O S O O

  22. 0.9 0.8 O O O 0.7 N 0.6 N M e N N d- 2 d- 0.5 O O O Fluorescence efficiency 0.4 N N N M e N 2 0.3 d+ H H d+ 0.2 0.1 0 12 2 4 6 8 10 pH

  23. Parallel Processing of Analog Sensory Information Sisira de Silva, Nalin Goonesekera, Suram Patuwathavithana, Sydney Ramyalal (Colombo) Nimal Gunaratne, Mark Lynch, Kemuel Nesbitt J. Am. Chem. Soc. 2007, 129, 3050

  24. Parallel processing to produce greatly increased dynamic range FLUOROPHORE SPACER SPACER FLUOROPHORE FLUOROPHORE SPACER SPACER FLUOROPHORE SIF RECEPTOR RECEPTOR RECEPTOR RECEPTOR 2 4 1 3 pH

  25. N R R 1 2 a ; R = R = CH CH 1 2 2 3 b ; R = R = CH CH OH 1 2 2 2 c ; R = H, R = CH CH N(CH CH ) 1 2 2 2 2 3 2 d ; R , R = CH CH N(CH )CH CH 1 2 2 2 3 2 2 N R R 1 2 Absorption l (log e) pKa Emission l (max , min) a 393(4.03), 372(4.02), 353(3.81) 405, 427, 445 (0.59, 0.004) 8.1 b 395(4.10), 374(4.09),355(3.87) 405, 427, 445 (0.56, 0.005) 6.1 c 395(4.03), 374(4.03),355(3.81) 404, 426, 443 (0.55, 0.014) 4.1 d 393(4.01), 372(4.01),353(3.76) 404, 426, 443 (0.56, 0.008) 1.4

  26. 100 100 SIF 80 60 0 SIF 390 Wavelength (nm) 500 40 20 0 10 2 6 4 8 0 pH

  27. Sensitive Molecular Thermometers Seiichi Uchiyama, Yuriko Matsumura Kaoru Iwai (Nara Women’s University) J. Mater. Chem. 2005, 15, 2796

  28. O C O N H i P r * N H * n H2O Increasing temperature O O Sensor exposed Sensor hidden N N O NIPAM N Co-polymerizable polarity sensor (Emission weakens in water) Temperature-sensitive polymer S O N M e 2 2

  29. IF 42 C 20 C 0 600 500 Wavelength (nm)

  30. C O N H i P r * * n IF NMe2 C O * * n 0 20 30 40 50 Temperature / C

  31. N H O 3:1 1:1 N H 1:3 3:1 O 1:1 10 O 1:3 IF N H 0 10 50 30 Temperature / oC

  32. Molecular Thermometry in a small space via FLIM 12 ns (33 oC) 100 mm 4 ns (31 oC) Intensity image Lifetime image Seiichi Uchiyama (Tokyo), Kaoru Iwai (Nara) Emmelyn Hughes & Anita Jones (Edinburgh) Steven Magennis (Manchester) Lab. Chip 2010, 10, 1267

  33. Arrival of Twisted Internal Charge Transfer (TICT) States in PET Systems n B u O N O N H M e N M e 2 Shuai Zheng, Tom Moody, Mark Lynch, Nimal Gunaratne, Terry Rice Photochem. Photobiol. Sci. 2012, 11, 1675

  34. .- n B u n B u O N O O N O . + N N H M e M e N M e N M e 2 2

  35. F = 0.031 .- n B u O N O pH Fluorescence Intensity F = 0.011 . + N M e 0 520 480 440 560 600 N M e Wavelength / nm 2

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