Triptycene 및 tetriptycene 구조를 갖는 새로운 silafluorene 유도체들의 합성과 이를 이용한 전기발광 특성 및 폭발물 센서에 관한 연구
- Issued Date
- 2016
- Abstract
- New functionalized Bis(triptycene)silafluorene and Bis(tetriptycene)silafluorene have been synthesized and their optical characterizations are investigated. silafluorene unit has been interested, since silafluorene has a unique optical and electronic properties. Here we report the synthesis of new type of photoluminescent Bis(triptycene)silafluorene and Bis(tetriptycene)silafluorene. New silafluorene have been characterized by FT-IR, TGA, LC-Mass and UV-vis absorption spectroscopy and X-ray single crystallography. Their optical characteristics have been also investigated using photoluminescence spectroscopy.
The synthesized compounds were characterized by 1H and 13C NMR spectroscopy. Absorption and emission spectra for these compounds were obtained by using UV-Visible and fluorescence spectroscopy in solution. Their emission behaviors and quantum yield for these compounds were investigated both in the solid and colloid state. Our results indicated that both compounds were used as the chemosensor to detect various type of explosives such as (1,3,5-trinitroperhydro -1,3,5-triazine, RDX), nitroaromatics (1,3,5-trinitrotoluene, TNT), and nitrate esters (PETN). The results of detection efficiency showed that both compounds were served as an excellent chemosensors and other metallafluorene derivatives were synthesized and their photonic behaviors were investigated.
Bis(triptycene) silafluorene and silafluorene are synthesized and evaluated for white O-LED applications. These compounds are of interest as light emissive layers, as they possess relatively low LUMO energy levels while maintaining high HOMO-LUMO optical gaps. Differential scanning calorimetry measurements reveal that these silafluorene compounds have advantages of thermal stability above 300 oC. Organic light-emitting diodes have been fabricated using thermal evaporation technique. They emit blue to bluish-white light with an excellent diode behavior under the forward bias.
- Alternative Title
- Novel Silafluorene Derivatives Having Triptycene and Tetriptycene Structures : Synthesis and Their Applications for Electroluminescence and Explosive Sensor.
- Alternative Author(s)
- Lee Sung Gi
- Affiliation
- 조선대학교 일반대학원
- Department
- 일반대학원 화학과
- Advisor
- 손홍래
- Awarded Date
- 2017-02
- Table Of Contents
- Novel Silafluorene Derivatives Having Triptycene and Tetriptycene Structures : Synthesis and Their Applications for Electroluminescence and Explosive Sensor.
Abstract......................................................................1
One. Synthesis and Optical Charactrization of Triptycene and Tetriptycene Silafluorene
1. Introduction................................................................3
2. Experimental Section..................................................6
2.1. Generals.................................................................6
2.2. Synthesis................................................................7
2.2.1. Preparation of1,2,4,5tetraboromobenzene1................7
2.2.2. Preparation of 2,3-dibromotriptycene 2.....................7
2.2.3. Preparation of 2,2-dibromobitriptycene 3...................8
2.2.4. Preparation of 1,1-methylhydro-4,5,8,9,-bis(triptycene)silafluorene 4................................................................8
2.2.5. Preparation of 1,1-dimethyl-4,5,8,9,-bis(triptycene)silafluorene 5................................................................9
2.2.6. Preparation of 1,1-dihydro-4,5,8,9-bis(triptycene)sillafluorene 6...............................................................9
2.2.7. Preparation of 1,1-diphenyl-4,5,8,9-bis(triptycene)sillafluorene 7..............................................................10
2.2.8. Preparation of spiro-4,5,8,9-bis(triptycene)silafluorene 8...............................................................10
2.2.9. Preparation of 1,1-dichloro-4,5,8,9-bis(triptycene)germafluorene 9...........................................................11
2.2.10. Preparation of 1,1-dimethyl-4,5,8,9-bis(triptycene)germafluorene 10..........................................................12
2.2.11. Preparation of 1,1-diphenyl-4,5,8,9-bis(triptycene)germafluorene 11.........................................................12
2.2.12. Synthesis of 6,7-Dibromo-1,4-dihydronaphthalene-1,4-epoxide 12.............................................................12
2.2.13. Synthesis of [1',2']Benzeno-5,14-dihydropentacene 13...............................................................................13
2.2.14. Synthesis of 2,3-diboromotetriptycene14...............13
2.2.15. Synthesis of 2,2-diboromobiteriptycene15.............14
2.2.16. Synthesis of 1,1-methylhydro-4,5,8,9-bis(tetriptycene)silafluorene 16..........................................14
2.2.17. Synthesis of 1,1-dimethyl-4,5,8,9-bis(tetriptycene)silafluorene 17.............................................................15
2.2.18. Synthesis of 1,1-dihydro-4,5,8,9-bis(tetriptycene)silafluorene 18.............................................................16
2.2.19. Synthesis of 1,1-diphneyl-4,5,8,9-bis(tetriptycene)silafluorene 19.............................................................17
3. Results and Discussion.............................................18
3.1. 센서 및 발광소재의 연구..........................................18
3.2. Preparation of Triptycenesilafluorene.......................19
3.3. Preparation of Triptycenegermafluorene...................25
3.4. Preparation of Tetriptycene silafluorene....................27
3.5. 단분자의 광학적 성질 (UV-Vis absorption and fluorescene spectra).....................................................32
3.6. LC-Mass...............................................................37
3.7. X-ray single crystal................................................44
3.8. TGA(Thermogravimetric Analysis) 측정 분석..............58
3.8.1. TGA 분석원리......................................................58
3.8.2. TGA에서 Mass change의 변화율calculation............59
3.8.3. TGA(Thermogravimetric Analysis) of Bis(tetriptycene)silafluorene..................................................................60
4. Conclusion...............................................................65
5. References...............................................................66
6. Spectrum.................................................................68
6.1. 1H NMR, 13C NMR spectroscopy.............................69
6.2. FT-IR....................................................................86
Two. Synthesis and Characterization of
Bis(triptycene)silafluorene Derivatives for Explosive Sensor.
1. Introduction..............................................................94
2. Experimental Section.................................................96
2.1.Generals................................................................96
2.2. Syntheses.............................................................97
2.2.1. Synthesis of Trinitrotoluen(TNT)............................97
2.2.2. Synthesis of Trimethylentrinitramin (RDX)..............98
2.2.3. Synthesis of Pentaerythritol tetranitrate(PETN).........99
2.2.4. Synthesis of 4,5,8,9-bis(triptycene)silafluorene ( Compound 4-7 ).......................................................100
2.2.5. Synthesis of 4,5,8,9-bis(teriptycene)silafluorene ( Compound 16-19 )......................................................101
3. Results and Discussion............................................102
3.1. Research of Sensor and Photoluminescence materials...................................................................102
3.2. Detection of Nitro compounds based on Triptycene metallafluorene..........................................................103
3.3. Quenching mechanism of Photoluminescence materials...................................................................104
3.4. Quenching PL Spectra Stern-Volmer plot of Bis(triptycene)silafluorene...............................................105
3.4.1. 1,1-dimethyhydro-4,5,8,9-bis(triptycene)silafluorene...............................................................106
3.4.2. 1,1-dimethy-4,5,8,9-bis(triptycene)silafluorene...............................................................108
3.4.3. 1,1-dihydro-4,5,8,9-bis(triptycene)silafluorene...............................................................110
3.4.4. 1,1-diphenyl-4,5,8,9-bis(triptycene)silafluorene...............................................................112
3.5.. Quenching PL Spectra Stern-Volmer plot of Bis(tetriptycene)silafluoren..............................................114
3.5.1. 1,1-dimethyhydro-4,5,8,9-bis(tetriptycene)silafluorene...............................................................115
3.5.2. 1,1-dimethy-4,5,8,9-bis(tetriptycene)silafluorene...............................................................117
3.5.3. 1,1-dihydro-4,5,8,9-bis(tetriptycene)silafluorene...............................................................119
3.5.4. 1,1-diphenyl-4,5,8,9-bis(tetriptycene)silafluorene................................................................121
4.Conclusions............................................................123
5. References.............................................................124
6. Spectrum................................................................126
6.1. 1H NMR, 13C NMR spectroscopy...........................127
Three. Optical Charaterization of Bis(triptycene)silafluorene as White Light Emitting Organic EL materials.
1. Introduction.............................................................130
2. Experiments...........................................................131
2.1. Generals..............................................................131
2.2. Syntheses............................................................132
2.2.1. Synthesis of 4,5,8,9-bis(triptycene)silafluorene ( Compound 4-7 )........................................................132
2.2.2. Synthesis of 4,5,8,9-bis(teriptycene)silafluorene ( Compound 16-19 ).....................................................133
2.2.3. Synthesis of silafluorene ( Compound 20-21 )........134
2.2.3.1. Preparation of 1,1-methylhydro-1-silafluorene 20.............................................................................135
2.2.3.2. Preparation of 1,1-dimethyl-1-silafluorene 21.............................................................................135
3. Results and Discussion............................................139
3.1. OLED (유기전기적발광소자) 원리......,......................139
3.2. OLED Device Materials..........................................140
3.3. Organic Light-emitting Diodes based on sillafluorene and Bis(triptycene)silafluorene.....................................143
3.3.1. Structure of OLED...............................................145
3.3.2. PL and EL spectra..............................................146
3.3.3. I-V-L 특성 분석...................................................148
3.4. Relative PL Quantum Yield Spectrometer.................150
3.5. Absolute PL Quantum Yield Spectrometer................155
4. Conclusion.............................................................157
5. References.............................................................158
- Degree
- Doctor
- Publisher
- 조선대학교 일반대학원
- Citation
- 이성기. (2016). Triptycene 및 tetriptycene 구조를 갖는 새로운 silafluorene 유도체들의 합성과 이를 이용한 전기발광 특성 및 폭발물 센서에 관한 연구.
- Type
- Dissertation
- URI
- https://oak.chosun.ac.kr/handle/2020.oak/13041
http://chosun.dcollection.net/common/orgView/200000265922
- Appears in Collections:
- General Graduate School > 4. Theses(Ph.D)
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Triptycene 및 tetriptycene 구조를 갖는 새로운 silafluorene 유도체들의 합성과 이를 이용한 전기발광 특성 및 폭발물 센서에 관한 연구.pdf
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