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PART 1. Porphyrin-Cored Arylether Dendrimers with Vinyl Groups in the Periphery 13

Abstract 14

I. 서론 15

1. Dendrimer란? 15

2. Dendrimer의 합성법 19

3. Dendrimer의 응용 20

4. 포르피린 (Porphyrin) 22

II. 실험 24

1. 시약 및 기기 24

2. 합성 26

III. 결과 및 고찰 63

1. 흡수 및 형광 스펙트럼 63

IV. 결론 72

V. 참고문헌 73

PART 2. A study on the synthesis of 2-Cyano-4'-methylbiphenyl 76

Abstract 77

I. 서론 78

II. 실험 81

1. 시약 및 기기 81

2. 합성 83

III. 결과 및 고찰 89

IV. 결론 99

V. 참고문헌 101

표목차

Part 1 12

Table 1. Absorption and fluorescence spectral data of dendrimers 1a-1c,... 65

Part 2 12

Table 1. Negishi coupling을 이용한 solvent 변화에 따른 합성 89

Table 2. Negishi coupling을 이용한 Lewis acid 변화에 따른 합성 91

Table 3. Kumada coupling을 기초로 Grignard reagent를 사용한 합성 93

Table 4. Sonogashira coupling을 토대로 ligand와 solvent 변화하여 합성 95

Table 5. Catalyst와 base를 변화하여 합성 97

그림목차

Part 1 8

Figure 1. 전형적인 dendrimer의 구조 15

Figure 2. 기능성 dendrimer의 종류: 성장과 정지세대를 반복하여... 16

Figure 3. Divergent 와 convergent approach 모식도 19

Figure 4. 약물전달체 시스템에 응용되는 dendrimer의 모식도 20

Figure 5. 촉매로써의 dendrimer 21

Figure 6. Chiral 구조의 dendrimer 21

Figure 7. MRI 영상진단에 사용되는 dendrimer 21

Figure 8. 킨바라 카즈시 강사와 아이다 타쿠죠 교수 연구팀이 개발한... 22

Figure 9. 홍색 광합성세균의 광포집 안테나 부분의 모식도 23

Figure 10. ¹H-NMR Spectra of dedrons Gn(3,5)-OH 34

Figure 11. ¹H-NMR Spectra of dendrimers 1a-1c 41

Figure 12. ¹H-NMR Spectra of dendrimers 2a-2c 46

Figure 13. ¹H-NMR Spectra of dendrimers 3a-3c 54

Figure 14. ¹H-NMR Spectra of dendrimers 4a-4c 62

Figure 15. Absorption spectra of free base porphyrin-cored arylether... 66

Figure 16. Absorption spectra of zinc porphyrin-cored arylether... 67

Figure 17. Fluorescence spectra of free base porphyrin-cored arylether... 68

Figure 18. Fluorescence spectra of free base porphyrin-cored arylether... 69

Figure 19. Fluorescence spectra of zinc porphyrin-cored arylether... 70

Figure 20. Fluorescence spectra of zinc porphyrin-cored arylether... 71

Part 2 9

Figure 1. ¹H-NMR spectrum of 2-Cyano-4'-methylbiphenyl 84

도식목차

Part 1 10

Scheme 1. Vögtle에 의해 합성된 "cascade molecule" 17

Scheme 2. Denkewalter에 의해 합성된 polypeptide dendrimer 18

Scheme 3. Poly(amidoamine) dendrimer 18

Scheme 4. Synthesis of dendrons Gn(3,5)-OH 26

Scheme 5. Synthesis of dendron G1(3,5)-CO₂CH₃ 27

Scheme 6. Synthesis of dendron G1(3,5)-OH 28

Scheme 7. Synthesis of dendron G2(3,5)-CO₂CH₃ 29

Scheme 8. Synthesis of dendron G2(3,5)-OH 30

Scheme 9. Synthesis of dendron G3(3,5)-CO₂CH₃ 31

Scheme 10. Synthesis of dendron G3(3,5)-OH 32

Scheme 11. Synthesis of arylether dendrimers 1a-1c with porphyrin in the... 35

Scheme 12. Synthesis of dendrimer TPP-G1 (1a) 36

Scheme 13. Synthesis of dendrimer TPP-G2 (1b) 37

Scheme 14. Synthesis of dendrimer TPP-G3 (1c) 39

Scheme 15. Synthesis of arylether dendrimers 2a-2c with zinc porphyrin... 42

Scheme 16. Synthesis of dendrimer ZnTPP-G1 (2a) 43

Scheme 17. Synthesis of dendrimer ZnTPP-G2 (2b) 44

Scheme 18. Synthesis of dendrimer ZnTPP-G3 (2c) 45

Scheme 19. Synthesis of arylether dendrimers 3a-3c with porphyrin in the... 47

Scheme 20. Synthesis of dendrimer TCPP-G1 (3a) 48

Scheme 21. Synthesis of dendrimer TCPP-G2 (3b) 50

Scheme 22. Synthesis of dendrimer TCPP-G3 (3c) 52

Scheme 23. Synthesis of arylether dendrimers 4a-4c with zinc porphyrin... 55

Scheme 24. Synthesis of dendrimer ZnTCPP-G1 (4a) 56

Scheme 25. Synthesis of dendrimer ZnTCPP-G2 (4b) 58

Scheme 26. Synthesis of dendrimer ZnTCPP-G3 (4c) 60

Part 2 11

Scheme 1. Tolylboronic acid 유도체인 고혈압치료제의... 79

Scheme 2. 2-Cyano-4'-methylbiphenyl을 합성하는 일반적 방법 79

Scheme 3. Negishi coupling을 이용한 solvent 변화에 따른 합성 83

Scheme 4. Negishi coupling을 이용한 Lewis acid 변화에 따른 합성 85

Scheme 5. Kumada coupling을 기초로 Grignard reagent를 사용한 합성 86

Scheme 6. Sonogashira coupling을 토대로 ligand와 solvent 변화하여 합성 87

Scheme 7. Catalyst와 base를 변화하여 합성 88

초록보기

PART 1 Porphyrin-Cored Arylether Dendrimers with Vinyl Groups in the Periphery

Benzyl aryl ether dendrimers with zinc porphyrin core and terminal vinyl groups have been synthesized and their photophysical properties and the influence of dendritic environments were investigated. Free base porphyrin-cored benzyl arylether dendrimers 1a-1c and 3a-3c, and their zinc derivatives 2a-2c and 4a-4c have been prepared. Absorption spectra are similar for all porphyrin-cored benzyl arylether dendrimers, except that absorption intensity at 280 nm increases in the higher generation of dendrimer. Fluorescence spectra are similar with two bands for all free-base porphyrin dendrimers 1a-1c and 3a-3c, although fluorescence intensity ratio of shorter wavelength emission band to longer wavelength band decreases with the generation of dendrimer. Emission efficiencies of zinc porphyrin dendrimers 2a-2c and 4a-4c are higher than that of ZnTTP and increase with dendrimer generation. Fluorescence spectra of 2c and 4c are red-shifted compared with other zinc porphyrin dendrimers.

PART 2 A study on the synthesis of 2-Cyano-4'-methylbiphenyl

2-Cyano-4'-methylbiphenyl is a useful intermediate for the production of a wide range of organic compounds. Especially in pharmaceutical chemistry, it is an important intermediate for the synthesis of various biologically active compounds, such as analgesics, antidepressants, antischizophrenia and antihypertensives.

The octapeptide angiontensin II produced by the reninangiotensin system (RAS) is a potent vasoconstrictor and thus plays an integral role in the pathophsiology of hypertension. Angiontensin II receptor antagonists have proved to lower blood pressure effectively, and better tolerated than other classes of drugs.

We report herein the synthetic method of 2-Cyano-4'-methylbiphenyl from the coupling reaction of corresponding aryl compounds.

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