Professor Chien-Tien Chen

1. 方泰山 教授榮退研討會 Doubly Ortho-linked Triarylethene, Hybrids for Chirochromic Optical Switch Applications Professor Chien-Tien Chen Department of Chemistry National Tsing Hua University

2. 學術研究的第一道光 (1986-1988) Oxa-di-pi-methane rearrangement It was damn difficult!!!

3. 學術研究的第二道光 (1998-) Triarylcarbenium Ions in Catalysis Asymmetric Mukaiyama Aldol Addition Asymmetric Allylation J. Am. Chem. Soc. 1997, 119, 11341. JOC1999, 64, 1090. Dibenzosuberene-based Helicenes as Chirochromic Optical Switches in LC Materials J. Am. Chem. Soc. 2000, 122, 7662-7672. Org. Lett.2010, 12,1472. Chem. Eur. J. 2010, 16, 12822 (frontispiece). Iminostilbene and Dibenzosuberene-based Spiro Bipolar Triarylamines and Tetraarylmethanes in Optoelectronic Applications J. Am. Chem. Soc. 2006, 128, 10992. J. Am. Chem. Soc. 2007, 129, 7478. J. Am. Chem. Soc. 2009, 131, 6698. Chem. Commun. 2011, feature article.

4. LC Chirochromic Switches with Binary Logic

5. Stacked Plot of CD Spectra for the Photoisomerization of (10R,11R)- Diethyl-DBS-based (P)-Helicene in Hexane at 280 nm [de]pss = (P – M’)/(P + M’) = [(eM’FM’→P - ePFP→M’)/(eM’FM’→P + ePFP→M’)] low FM’→P isodichroic isodichroic JACS 2000, 122 (32), 7662.

6. Droplets of K-15 containing (left) 1% (10R,11R,P) (right) 1% (10R,11R,M’) suspended in glycerol viewed at 200x magnification at room temperature p: Distance between concentric rings

7. Modulation of Photoswitching Profiles by 10,11-Dialkoxymethyl Substituents in C2-Symmetric DBS-based Helicenes spin-orbit perturbation FM’→P ~ FP→M’ better solubility in LC Chen, C.-T.; * Chen, W.-C.; Lin, B.-C. Chem. Eur. J. 2010, 16, 12822 as a frontispiece.

8. LC Optical Switch with Ternary Logic N*-LC (R,R,P)6c N*-LC (R,R,P)6c Standard LC Standard LC 290 nm 200 mm 200 mm A B 330 nm 310 nm 310 nm 310 nm 200 mm 200 mm C D p= 8.2 mm p= 13.9 mm p = 2 × L × tan q 200 m m m m p= 16.3mm p ~ 0mm

9. Photoswitching Profiles by 10,11-Dialkoxymethyl Substituents in C2-Symmetric DBS-based Helicenes Bearing Flexible Axial Chirality

10. Helicene/Azobenzene Hybrid System as a Dual-mode Synergistic Optical Switch

11. Chirochromic Switching Chen, C.-T.; * Chen, W.-C. Org. Lett. 2010, 12, 1472.

12. Summary Ternary logic Dual mode • 高的非鏡像選擇性(P/M’, ＜1/＞99 to 96/4) • 將螺旋稀化合物摻雜於向列相液晶E7中，能夠誘導生成膽固醇相液 • 晶，並且可以藉由光異構化反應可以調控膽固醇相液晶的螺距及相對 • 手性，成為具有三元邏輯的開關記憶材料。 • 增加C10和C11位置取代基的立體效應，增加其在近軸向構型的穩定 • 性，而大幅增加其光學切換的選擇性，有增效作用。

13. Molecular Design for cis-STIF Trimer Systems STIF as el. accepting template

14. Time Resolved Transient Absorption Spectra in Ar-saturated DCE, DMF, and Bz By Wei, Y.; Chen, C.-T.*; and Majima, T.* et al. JACS 2009, 131, 6698. [a]Measured in DCE. [b] The data in parentheses correspond to half-lives (ms). [c] Measured in DMF. [d] Measured in bz (the total amount of emission relative to that of 12 is 100%). [e] The data in parentheses correspond to full width at half-maximum.

15. Comparison Among Spiro-STIF Fused Systems

16. Comparison between Spiro-Fluorene and Spiro-STIF Fused Systems PEDOT EML TPBi lmax: 468 (76); with host CBP (10 wt%) Fext: 2.5% hc: 5.2 cd/A; hp: 2.7 lm/w Lmax: 5494 cd/m2 2.3 2.7 5.0 6.2 lmax: 445 (81); Trilayer device Fext: 4.5% hc: 9.2 cd/A; hp: 3.0 lm/w L20: 1847 cd/m2

17. Future Outlooks

18. 那個光的故事

19. Acknowledgments Collaborator: Prof. Yu-Tai Tao (Academia Sinica) Prof. Testsuro Majima (ISIR, Osaka Univ.) Prof. Eiichi Nakamura (Univ. of Tokyo) Dr. Yi Wei Mr. Wei-Shang Chao Mr. How-wei Liu Dr. Bor-Chiao Lin Mr. Wen-Ching Chen Mr. Chien-Hsiang Chen Financial Supports: National Science Council Department of Chemistry National Taiwan Normal University National Tsing-Hua University

20. 結語和祝語