Institute of Chemistry, Academia Sinica

material science. We have uncovered two very useful reactions to construct acene structures.
We have also synthesized a series compounds with potential to for acene based self-assembly monolayer (SAM) on gold surface.
Ether-Ether and Ether-Sulfide Exchange Reaction on Acene Structures
An Iterative Synthesis of Various Acene Structures
Various Protected Acene Thiols for Construction of SAM

1. Lin, K.-H.; Pal, B.; Tsou, L.-D.; Lin, C.-H. Iterative Synthesis of Acene via Homo-elongation. Chem. Comm. 2009, 803.
2. Chen, J.-C.; Lee, T.-S.; Lin, C.-H. Syntheses of Ladder-Type Oligonaphthalene Derivatives and Their Photophysical and Electrochemical Properties. Chem. Eur. J. 2008, 14, 2777.
3. Tseng, Y. P.; Kuo, Y. H.; Hu, C. P.; Jeng, K. S.; D. Janmanchi, D.; Lin, C. H.; Chou, C. K.; Yeh, S. F. The Role of Helioxanthin in Inhibiting Human Hepatitis B Viral Replication and Gene Expression by Interfering with the Host Transcrioptional Machinery. Antiviral Res. 2008, 77, 206.
4. Tseng, P.-C.; Hsu, H.-C.; Janmanchi, D.; Lin, C.-H.; Kuo, Y.-H.; Chou, C.-K.; Yeh, S.-F. The Role of Helioxanthin in Inhibiting Interleukin-1β-induced MIP-1β Production in Human Hepatoma Cells by Reduction of c-Jun Expression and Subsequent Binding of the c-jun/CREB1 Complex to the AP-1/CRE Site of the MIP-1β Promoter. Biochem. Pharma. 2008, 76, 1121.
5. Lin, Y. C.; Lin, C. H. Synthesis of tetracene sulfoxide and tetracene sulfone via a cascade cyclization reaction. Org. Lett. 2007, 9, 2075.
6. Yang, H.-C.; Lin, S.-M.; Liu, Y.-H.; Wang, Y.; Chen, M.-M.; Sheu, H.-S.; Tsou, D.-L.; Lin, C-H.; Luh, T.-Y. Ring Opening Metathesis Polymerization of Bisnorbornene Derivatives Linked by Cp2Ni2(m-S)2 Bridge. J. Organometallic Chem. 2006, 691, 3196.
7. Radhakrishnan K; Lin, C-H. Synthesis of anthryl sulfides from anthryl methyl ethers via acid-catalyzed ether-sulfide exchange reaction. Synlett 2005, 14, 2179
8. Lin, C-H.; Radhakrishnan K. Synthesis of anthracene ethers from anthracene methyl ethers via an acid-catalyzed exchange reaction. Chem. Comm. 2005, 4, 504
9. Lin, C-H.; Tour, J. Hydrogen-Bond-Assisted p-Stacking of Shape-Persistent Cyclophanes. J. Org. Chem. 2002, 67, 7761.

Update： 2023-11-08

1. Ting-Yu Li, Yi-Chun Lin, Yu-Huei Song, Hsiu-Feng Lu, Ito Chao*, Chih-Hsiu Lin* Synthesis and Physical Study of Perylene and Anthracene Polynitrile as Electron Acceptors. Organic Letters 2019-07-19, 21(14) 5397-5401.
2. Jhih-Liang Huang, BillaBhargava Rao, Manyam Praveen Kumar, Hsiu-Feng Lu, Ito Chao*, Chih-Hsiu Lin* Dicyclopenta[ghi,pqr]perylene as a Structural Motif for Bowl-Shaped Hydrocarbons: Synthetic and Conformational Studies. Organic Letters 2019-04-19, 21(8) 2504-2508.
3. Bikash Pal, Chun-Hsiung Chang, Cian-Jhe Zeng, Chih-Hsiu Lin* Template-Assisted Benzannulation Route to Pentacene and Tetracene Derivatives and its Application to Construct Amphiphilic Acenes That Self-Assemble into Helical Wires. Chemistry - A European Journal 2017-12-01, 23(69) 17542-17548.
4. Bikash Pal, Bo-Chao Lin, Mark Vincent Carreon dela Cerna, Chao-Ping Hsu*, Chih-Hsiu Lin* Face-to-Face Packing of 2,3,9,10-Tetrasubstituted Pentacene Derivatives Revealed through a Solid State [4 + 4] Thermal Cycloaddition and Molecular Dynamic Simulation. The Journal of Organic Chemistry 2016-08-05, 81(15) 6223-6234.
5. Chih-Hsiu Lin, Gregory S. Ferguson, Manoj K. Chaudhury* Electrokinetics of polar liquids in contact with nonpolar surfaces.. Langmuir : the ACS journal of surfaces and colloids 2013-06-25, 29(25), 7793-801.
6. Damodar Janmanchi, Chih Hsiu Lin*, Jui-yu Hsieh, Ya-ping Tseng, Tai-an Chen, Hong-jhih Jhuang, Sheau Farm Yeh* Synthesis and biological evaluation of helioxanthin analogues. Bioorganic & Medicinal Chemistry 2013-04-01, 21, 2163-2176.
7. Billa Bhargava Rao , Jun-Ru Wei , and Chih-Hsiu Lin, New Synthetic Routes to Z-Shape Functionalized Perylenes. ORGANIC LETTERS 2012-06, 14, 3640-3643.
8. Yi-Chun Lin , Chih-Hsiu Lin , Chan-Yu Chen , Shih-Sheng Sun and Bikash Pal Synthesis of electron deficient acene derivatives via a bidirectional iterative elongation reaction. ORGANIC & BIOMOLECULAR CHEMISTRY 2011-04, 9,4507-4517.
9. Damodar Janmanchi, Ya Ping Tseng, Kuei-Chen Wang, Ray Ling Huang, Chih Hsiu Lin, Sheau Farn Yeh Synthesis and the biological evaluation of arylnaphthalene lignans as anti-hepatitis B virus agents. BIOORGANIC & MEDICINAL CHEMISTRY 2010-02, 18,1213-1266.
10. Chih-hsiu Lin, Tong-Tsou Hsu Synthesis of Benzo[c] and Naphtho[c]heterocycle Diesters and Dinitriles via Homoelongation. JOURNAL OF ORGANIC CHEMISTRY 2009-11, 74 (23), 9180-9187.
11. Ke-Han Lin, Bikash Pal, Li-Der Tsou, Chih-Hsiu Lin* Iterative synthesis of acenes via homo-elongation . Chem.Comm. 2009-02, 803-805.
12. Pei-Chi Tseng, Hsing-Chih Hsu, Damodar Janmanchi, Chih-Hsiu Lin, Yueh-Hsiung Kuo, Chen-Kung Chou* Sheau-Farn Yeh* The Role of Helioxanthin in Inhibiting Interleukin-1β-induced MIP-1β Production in Human Hepatoma Cells by Reduction of c-Jun Expression and Subsequent Binding of the c-jun/CREB1 Complex to the AP-1/CRE Site of the MIP-1β Promoter. Biochem. Pharma. 2008-10, 76, 1121-1133.
13. Y. P. Tseng, Y. H. Kuo, C. P. Hu, K. S. Jeng, D. Janmanchi, C. H. Lin, C. K. Chou* S. F. Yeh* The role of helioxanthin in inhibiting human hepatitis B viral replication and gene expression by interfering with the host transcrioptional machinery . Antiviral Res. 2008-05, 77, 206-214.
14. Jun-Chun Chen, Tsi-Shi Lee, Chih-Hsiu Lin* Syntheses of Ladder-Type Oligonaphthalene Derivatives and Their Photophysical and Electrochemical Properties. CHEMISTRY-A EUROPEAN JOURNAL 2008-02, 14, 2777-2787.
15. Yi-Chun Lin, Chih-Hsiu Lin* Synthesis of tetracene sulfoxide and tetracene sulfone via a cascade cyclization reaction. Org. Lett. 2007-04, 9, 2075-2078.
16. Yang, HC, Lin, SM, Liu, H, Wang, Y, Chen, MM, Sheu, HS, Tsou, DL, Lin, CH and Luh, TY Ring opening metathesis polymerization of bisnorbornene derivatives linked by Cp2Ni2(mu-S)(2) bridge. JOURNAL OF ORGANOMETALLIC CHEMISTRY 2006-07, 691(14), 3196-3200.
17. C-H Lin* and K. Radhakrishnan Synthesis of anthracene ethers from anthracene methyl ethers via an acid-catalyzed exchange reaction.. Chem. Comm. 2005, 4, 504-506.
18. K. Radhakrishnan and C.-H. Lin* Synthesis of anthryl sulfides from anthryl methyl ethers via acid-catalyzed ether-sulfide exchange reaction.. Synlett 2005, 14, 2179-2182.