Synthesis and optical characteristics of organic light-emitting dot based on well-defined octa-functionalized silsesquioxane
Source abstract
Abstract
This article reports the synthesis and characterization of a quantum-confined luminescent dot with size 2–3 nm using well-defined m-octa(bromophenyl) silsesquioxane (m-OBPS) as core. The highly regioselective bromination of octaphenylsilsesquioxane (OPS), which is an electron-deficient nanometer-sized molecule, has been synthesized using combined catalyst of iodine and zinc chloride at room temperature in dichloromethane solvent. Based on m-OBPS, a hybrid luminescent dot with well-defined structure was synthesized. UV absorption and PL spectra of this light-emitting dot remain same in dilute solution, condensed state, and solid solution. Furthermore, time-resolved PL study indicates that the exciton decay time of the light-emitting dot remains similar regardless in dilute solution, condensed state, or blended with other polymers, suggesting that the charge carriers are well confined within the individual light-emitting dot due to the unique star-like structure and shielding alkyl chain layer. The light-emitting nano-particles can be considered as isolated chromophores as both inter- and intra- molecular aggregation are prohibited.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Silicone and Siloxane Chemistry · Luminescence and Fluorescent Materials · Organic Light-Emitting Diodes Research
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (38)
Show source-provided references
1. Brown HC, Pearsall HW (1952) The action of the catalyst couple aluminum chloride-hydrogen chloride on toluene at low temperatures—The nature of Friedel-crafts complexes. J Am Chem Soc 74(1):191–19510.1021/ja01121a049 ↗
2. Cheng CC, Chien CH, Yen YC, Ye YS, Ko FH, Lin CH, Chang FC (2009) A new organic/inorganic electroluminescent material with a silsesquioxane core. Acta Mater 57(6):1938–194610.1016/j.actamat.2008.12.031 ↗
3. Cho HJ, Hwang DH, Lee JI, Jung YK, Park JH, Lee J, Lee SK, Shim HK (2006a) Electroluminescent polyhedral oligomeric silsesquioxane-based nanoparticle. Chem Mater 18(16):3780–378710.1021/cm061011f ↗
4. Cho HM, Weissman H, Wilson SR, Moore JS (2006b) A Mo(VI) alkylidyne complex with polyhedral oligomeric silsesquioxane ligands: homogeneous analogue of a silica-supported alkyne metathesis catalyst. J Am Chem Soc 128(46):14742–1474310.1021/ja065101x ↗
5. Choi J, Harcup J, Yee AF, Zhu Q, Laine RM (2001) Organic/inorganic hybrid composites from cubic silsesquioxanes. J Am Chem Soc 123(46):11420–1143010.1021/ja010720l ↗
6. Chou CH, Hsu SL, Dinakaran K, Chiu MY, Wei KH (2005a) Synthesis and characterization of luminescent polyfluorenes incorporating side-chain-tethered polyhedral oligomeric silsesquioxane units. Macromolecules 38(3):745–75110.1021/ma0479520 ↗
7. Chou CH, Hsu SL, Yeh SW, Wang HS, Wei KH (2005b) Enhanced luminance and thermal properties of poly(phenylenevinylene) copolymer presenting side-chain-tethered silsesquioxane units. Macromolecules 38(22):911–9123
8. Chua LL, Zaumseil J, Chang JF, Ou ECW, Ho PKH, Sirringhaus H, Friend RH (2005) General observation of n-type field-effect behaviour in organic semiconductors. Nature 434(7030):194–19910.1038/nature03376 ↗
9. Daniel C, Makereel F, Herz LM, Hoeben FJM, Jonkheijm P, Schenning APHJ, Meijer EW, Friend RH, Silva C (2005) The effects of supramolecular assembly on exciton decay rates in organic semiconductors. J Chem Phys 123(8):08490210.1063/1.1998828 ↗
10. Dewar MJS (1946) The kinetics of some benzidine rearrangements, and a note on the mechanism of aromatic substitution. J Chem Soc 1946:777–78110.1039/jr9460000777 ↗
11. Erben C, Grade H, Goddard GD (2006) Bromination of octaphenylsilsesquioxane. Silicon Chem 3:43–4910.1007/s11201-005-9000-5 ↗
12. Fakis M, Polyzos I, Tsigaridas G, Giannetas V, Persephonis P (2004) Excited state dynamics of a partially conjugated polymer studied by feratosecond fluorescence upconversion spectroscopy. Chem Phys Lett 394(4–6):372–37610.1016/j.cplett.2004.07.030 ↗
13. Froehlich JD, Young R, Nakamura T, Ohmori Y, Li S, Mochizuki A, Lauters M, Jabbour GE (2007) Synthesis of multi-functional POSS emitters for OLED applications. Chem Mater 19(20):4991–499710.1021/cm070726v ↗
14. Gnanapragasam NS, Ramanujam R, Srinivasan SP (1976) Bromination of acetanilide catalyzed by anhydrous ferric-chloride, anhydrous zinc-chloride and iodine bromide. Curr Sci 45(24):862–863
15. He CB, Xiao Y, Huang JC, Lin TT, Mya KY, Zhang XH (2004) Highly efficient luminescent organic clusters with quantum dot-like properties. J Am Chem Soc 126(25):7792–779310.1021/ja049650j ↗
16. Herland A, Bjork P, Nilsson KPR, Olsson JDM, Asberg P, Konradsson P, Hammarstrom P, Inganas O (2005) Electroactive luminescent self-assembled bio-organic nanowires: integration of semiconducting oligoelectrolytes within amyloidogenic proteins. Adv Mater 17(12):1466–147110.1002/adma.200500183 ↗
17. Kang JM, Cho HJ, Lee J, Lee JI, Lee SK, Cho NS, Hwang DH, Shim HK (2006) Highly bright and efficient electroluminescence of new PPV derivatives containing polyhedral oligomeric silsesquioxanes (POSSs) and their blends. Macromolecules 39(15):4999–500810.1021/ma0603377 ↗
18. Laine RM, Choi JW, Lee I (2001) Organic-inorganic nanocomposites with completely defined interfacial interactions. Adv Mater 13(11):800–80310.1002/1521-4095(200106)13:11<800::AID-ADMA800>3.0.CO;2-G ↗
19. Lee J, Cho HJ, Jung BJ, Cho NS, Shim HK (2004) Stabilized blue luminescent polyfluorenes: introducing polyhedral oligomeric silsesquioxane. Macromolecules 37(23):8523–852910.1021/ma0497759 ↗
20. Lickiss PD, Rataboul F (2008) Fully condensed polyhedral oligosilsesquioxanes (POSS): from synthesis to application. Adv Organomet Chem 57:1–11610.1016/S0065-3055(08)00001-4 ↗
21. Lim TS, Hsiang JC, White JD, Hsu JH, Fan YL, Lin KF, Fann WS (2007) Single short-chain conjugated polymer studied with optical spectroscopy: a donor-accepter system. Phys Rev B 75(16):16520410.1103/PhysRevB.75.165204 ↗
22. Lin WJ, Chen WC, Wu WC, Niu YH, Jen AKY (2004) Synthesis and optoelectronic properties of starlike polyfluorenes with a silsesquioxane core. Macromolecules 37(7):2335–234110.1021/ma0499573 ↗
23. Liu YL, Lee HC (2006) Preparation and properties of polyhedral oligosilsequioxane tethered aromatic polyamide nanocomposites through Michael addition between maleimide-containing polyamides and an amino-functionalized polyhedral oligosilsequioxane. J Poly Sci A Poly Chem 44(15):4632–464310.1002/pola.21562 ↗
24. Liu J, Shi YJ, Yang Y (2001) Improving the performance of polymer light-emitting diodes using polymer solid solutions. App Phys Let 79(5):578–58010.1063/1.1389324 ↗
25. Lo SC, Burn PL (2007) Development of dendrimers: macromolecules for use in organic light-emitting diodes and solar cells. Chem Rev 107(4):1097–111610.1021/cr050136l ↗
26. Lo MY, Zhen CG, Lauters M, Jabbour GE, Sellinger A (2007) Organic-inorganic hybrids based on pyrene functionalized octavinylsilsesquioxane cores for application in OLEDs. J Am Chem Soc 129(18):5808–580910.1021/ja070471m ↗
27. Miyake J, Chujo Y (2008) A hybrid-type, chiral pi-conjugated polymer wrapped with polyhedral oligomeric silsesquioxanes. J Polym Sci A Polym Chem 46(18):6035–604010.1002/pola.22914 ↗
28. Niu YH, Huang J, Cao Y (2003) High-efficiency polymer light-emitting diodes with stable saturated red emission: use of carbazole-based copolymer blends in a poly(p-phenylenevinylene) derivative. Adv Mater 15(10):807–81110.1002/adma.200304619 ↗
29. Olah GA (1971) Aromatic substitution. 28. Mechanism of electrophilic aromatic substitutions. Acc Chem Res 4(7):24010.1021/ar50043a002 ↗
30. Olah GA, Bucsi I, Lambert C, Aniszfeld R, Trivedi NJ, Sensharma DK, Prakash GKS. J (1991) considered polycarbon supercage chemistry .2. Chlorination and bromination of fullerenes—nucleophilic methoxylation of polychlorofullerenes and their aluminum trichloride catalyzed Friedel-crafts reaction with aromatics to polyarylfulle. Am Chem Soc 113(24):9385–938710.1021/ja00024a063 ↗
31. Samuel IDW, Rumbles G, Collison CJ, Friend RH, Moratti SC, Holmes AB (1997) Picosecond time-resolved photoluminescence of PPV derivatives. Syn Met 84(1–3):497–50010.1016/S0379-6779(97)80837-5 ↗
32. Sellinger A, Tamaki R, Laine RM, Ueno K, Tanabe H, Williams E, Jabbour GE (2005) Heck coupling of haloaromatics with octavinylsilsesquioxane: solution processable nanocomposites for application in electroluminescent devices. Chem Commun 29:3700–370210.1039/b505048k ↗
33. Su RQ, Muller TE, Prochazka J, Lercher JA (2002) A new type of low-kappa dielectric films based on polysilsesquioxanes. Adv Mater 14(19):1369–137310.1002/1521-4095(20021002)14:19<1369::AID-ADMA1369>3.0.CO;2-I ↗
34. Tonzola CJ, Alam MM, Bean BA, Jenekhe SA (2004) New soluble n-type conjugated polymers for use as electron transport materials in light-emitting diodes. Macromolecules 37(10):3554–356310.1021/ma035971o ↗
35. Xiao S, Nguyen M, Gong X, Cao Y, Wu HB, Moses D, Heeger AJ (2003) Stabilization of semiconducting polymers with silsesquioxane. Adv Funct Mater 13(1):25–2910.1002/adfm.200390000 ↗
36. Xiao Y, Liu L, He CB, Chin WS, Lin TT, Mya KY, Huang JC, Lu XH (2006) Nano-hybrid luminescent dot: synthesis, characterization and optical properties. J Mater Chem 16(9):829–83610.1039/B510666D ↗
37. Xiong SX, Xiao Y, Ma J, Zhang LY, Lu XH (2007) Enhancement of electrochromic contrast by tethering conjugated polymer chains onto polyhedral oligomeric silsesquioxane nanocages. Macromol Rapid Commun 28(3):281–28510.1002/marc.200600717 ↗
38. Yeddanapalli LM, Gnanapragasam NS (1956) Kinetics and mechanism of bromination of phenol with bromine and iodine bromide in glacial acetic acid and carbon tetrachloride. J Chem Soc Dec 4934–494310.1039/jr9560004934 ↗