Donor-acceptor compound based on rhodanineacetic acid-pyrene derivative: Red-light emitting fluorescent organic nanoparticles

Journal of Fluorescence

Volumn 22, Issue 1, 2012, Pages 1-7

  Zhang, Bo ^a   Diao, Wei ^a   Bi, Chun ^a   Sun, Jian ^a   Han, Guoxia ^a   Shi, Yi ^a   Sheng, Li ^a   Yin, Gui ^a   Pu, Lin ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

Donor acceptor compound; Fluorescent organic nanoparticles; Red shift; Sensibility; Vapor experiment

Indexed keywords

DONOR-ACCEPTOR COMPOUNDS; EMISSION SPECTRUMS; FLUORESCENCE SWITCHING; MEAN DIAMETER; METHANOL SOLUTION; ORGANIC NANOPARTICLES; ORGANIC VAPORS; PLANARIZATION; RED SHIFT; RED-SHIFTED; REPRECIPITATION METHODS; SEM AND TEM; SENSIBILITY;

EMISSION SPECTROSCOPY; EXPERIMENTS; METHANOL; NANOPARTICLES; PROFITABILITY; SURFACE ACTIVE AGENTS; VAPORS;

FLUORESCENCE;

ACETIC ACID; NANOPARTICLE; PYRENE; PYRENE DERIVATIVE; RHODANINE;

ABSORPTION; ARTICLE; CHEMISTRY; COLOR; PARTICLE SIZE; SPECTROFLUOROMETRY; VOLATILIZATION;

ABSORPTION; ACETIC ACID; COLOR; NANOPARTICLES; PARTICLE SIZE; PYRENES; RHODANINE; SPECTROMETRY, FLUORESCENCE; VOLATILIZATION;

EID: 84857640624     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-011-0951-y     Document Type: Article

References (36)

1. Empedocles SA, Bawendi MG (1997) Quantum-confined stark effect in single CdSe nanocrystallite quantum dots. Science 278 (5346):2114-2117 (Pubitemid 28028319)
2. Alivisatos AP (1996) Semiconductor clusters nanocrystals and quantum dots. Science 271(5251):933-937 (Pubitemid 126554899)
3. Hagfeldt A, Gratzel M (1995) Light-induced redox reactions in nanocrystalline systems. Chem Rev 95(1):49-68
4. Schlamp MC, Peng X, Alivisatos AP (1997) Improved efficiencies in light emitting diodes made with CdSe(CdS) core/shell type nanocrystals and a semiconducting polymer. J Appl Phys 82 (11):5837-5842 (Pubitemid 127584784)
5. An BK, Kwon SK, Jung SD, Park SY (2002) Enhanced emission and its switching in fluorescent organic nanoparticles. J Am Chem Soc 124(48):14410-14415 (Pubitemid 35407451)
6. Kasai H, Kamatani H, Okada S, Nakanishi H et al (1996) Size-dependent colors and luminescences of organic microcrystals. Jpn J Appl Phys 35:L221-L223
7. Kasai H, Kamatani H, Yoshikawa Y, Nakanishi H et al (1997) Crystal size dependence of emission from perylene microcrystals. Chem Lett 26:1181-1182
8. Kasai H, Yoshikawa Y, Seko T, Nakanishi H et al (1997) Optical properties of perylene microcrystals. Mol Cryst Liq Cryst 294:173-175
9. Komai Y, Kasai H, Hirakoso H, Nakanishi H et al (1998) Size and form control of titanylphthalocyanine microcrystals by supercritical fluid crystallization method. Mol Cryst Liq Cryst 322:167-169
10. Yeh HC, Yeh SJ, Chen CT (2003) Readily synthesised arylamino fumaronitrile for non-doped red organic light-emitting diodes. Chem Comm 39:2632-2633
11. Chen CT (2004) Evolution of red organic light-emitting diodes: materials and devices. Chem Mater 16(23):4389-4400
12. Palayangoda SS, Cai XC, Adhikari RM, Neckers DC (2008) Carbazole-based donor-acceptor compounds: highly fluorescent organic nanoparticles. Org Lett 10(2):281-284
13. Chen J, Xu B, Ouyang X, Cao Yet al (2004) Aggregation-induced emission of cis, cis-1,2,3,4-tetraphenylbutadiene from restricted intramolecular rotation. J Phys Chem A 108(37):7522-7524
14. Winnick FM (1993) Photophysics of preassociated pyrenes in aqueous polymer solutions and in other organized media. Chem Rev 93(2):587-614
15. Nishizawa S, Kato A, Teramae N (1999) Fluorescence sensing of anions via intramolecular excimer formation in a pyrophosphate-induced self-assembly of a pyrene-functionalized guanidinium receptor. J Am Chem Soc 121:9463-9464 (Pubitemid 29485304)
16. Sahoo D, Narayanaswami V, Kay CM, Ryan RO (2000) Pyrene excimer fluorescence: a spatially sensitive probe to monitor lipid-induced helical rearrangement of apolipophorin III. Biochemistry 39(22):6594-6601 (Pubitemid 30353991)
17. Kim JS, Noh KH, Lee SH, YoonJetal(2003) Molecular Taekwondo. 2. A new calix[4]azacrown bearing two different binding sites as a new fluorescent ionophore. J Org Chem 68(2):597-600 (Pubitemid 36125997)
18. Yuasa H, Miyagawa N, Izumi T, Hashimoto H (2004) Hinge sugar as a movable component of an excimer fluorescence sensor. Org Lett 6(9):1489-1492 (Pubitemid 38626336)
19. Wang YH, Li B, Zhang LM, Li P et al (2010) A highly selective regenerable optical sensor for detection of mercury(II) ion in water using organic-inorganic hybrid nanomaterials containing pyrene. New J Chem 34:1946-1953
20. Huo C, Chambron JC, Meyer M (2008) Dual emission of a bis (pyrene)-functionalized, perbenzylated β-cyclodextrin. New J Chem 32:1536-1542
21. Xu ZC, Singh NJ, Lim J, Yoon J et al (2009) Unique sandwich stacking of pyrene-adenine-pyrene for selective and ratiometric fluorescent sensing of ATP at physiological pH. J Am Chem Soc 131(42):15528-15533
22. Zhou Y, Kim JW, Yoon J et al (2010) Novel bi-nuclear boron complex with pyrene ligand: red-light emitting as well as electron transporting material in organic light-emitting diodes. Org Lett 12 (6):1272-1275
23. Wu W, Wu W, Ji S, Zhao J et al (2010) Observation of room-temperature deep-red/near-IR phosphorescence of pyrene with cycloplatinated complexes: an experimental and theoretical study. Eur J Inorg Chem 4470-4482
24. Zhang B, Sun J, Yin G, Pu L et al (2011) A highly selective ratiometric fluorescent chemosensor for Ag+ based on a rhodani-neacetic acid-pyrene derivative. New J Chem 35:849-853
25. Horn D, Rieger J (2001) Organic nanoparticles in the aqueous phase- theory, experiment, and use. Angew Chem Int Ed 40(23):4330-4361 (Pubitemid 33150759)
26. Tong H, Dong Y, Häußler M, Tang BZ et al (2006) Tunable aggregation-induced emission of diphenyldibenzofulvenes. Chem Commun 42(10):1133-1135 (Pubitemid 43344119)
27. Upamali KAN, Estrada LA, De PK, Neckers DC et al (2011) Carbazole-based cyano-stilbene highly fluorescent microcrystals. Langmuir 27(5):1573-1580
28. Gruszecki WI (1999) Light-induced excitation quenching and structural transition in light-harvesting complex II. J Biol Phys 59:175-185 (Pubitemid 29326328)
29. Birks JB (1970) Photophysics of aromatic moelcules. Wiley, London
30. Baker KN, Farmer AV, Resch T, Farmer BL et al (1993) Crystal structures, phase transitions and energy calculations of poly(p-phenylene) oligomers. Polymer 34(8):1571-1587
31. Guha S, Graupner W, Resel R, Leising G et al (1999) Planarity of para hexaphenyl. Phys Rev Lett 82(18):3625-3628 (Pubitemid 129689282)
32. Tian B, Zerbi G, Müllen K (1991) Electronic and structural properties of polyparaphenylenevinylene from the vibrational spectra. J Chem Phys 95:3198-3207
33. Lagowski JB (2002) Ab initio investigation of conformational and excitation energies of phenylene vinylene oligomers. J Mol Struct 589:125-137
34. Woo HS, Lhost O, Graham SC, Müllen K et al (1993) Optical spectra and excitations in phenylene vinylene oligomers. Synth Met 59(1):13-28
35. +-selective ratiometric and "Off-On" chemosensor based on the azadiene -pyrene derivative. Org Lett 12(11):2566-2569
36. Auweter H, Haberkorn H, Heckmann W, Weiss H et al (1999) Supramolecular structure of precipitated nanosize /3-carotene particles. Angew Chem Int Ed 38(15):2188-2191 (Pubitemid 29391842)