Final Report for Grant "Direct Writing via Novel Aromatic Ladder Polymer Precursors" Page: 3 of 17
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Scheme I. Proposed Route to an aromatic ladder polymer amenable to photolithographic patterning.
CN CN CN CN CN CN CN CN CN
X e Polymerize X CN
SieSitel of "A" site w. n
R "B" site R R R R
N -N N N N N N(H)
X = Br, Cl, I
R = various Cyclize X I I CN
- Solubilizing group
-Electron donating group n
- Electron withdrawing group R R R R
H H H
N N N N N N(H)
Tautomerize X CN
n
R R R R
We have published four contributions as the result of the work in this grant:
1. "Cascade cyclization to produce a series of fused, aromatic molecules" Behof, W. J.;
Wang, D.; Niu, W.; Gorman, C. B. Org. Lett., 2010, 12 (9), 2146-2148 (Selected as
SynFact of the month: Synfacts 2010, 7, 0763-0763)
2. "Aminoisoquinolines as Colorimetric Hg2+ Sensors: The Importance of Molecular
Structure and Sacrificial Base" Wan, Y.; Niu, W.; Behof, W. J.; Wang, Y.; Boyle, P.,
Gorman, C. B. Tetrahedron, 2009, 65, 4293-4297.
3. "Efficient synthesis of halo indanones via chlorosulfonic acid mediated Friedel-Craft
cyclization of aryl propionic acids and their use in alkylation reactions" Sharma, A.
K.; Subramani, A. V.; Gorman, C. B. Tetrahedron 2007, 63, 389-395.
4. "Chlorosulfonic Acid" Sharma, A. K.; Gorman, C. B. in e-EROS Encyclopedia of
Reagents for Organic Synthesis, Paquette, L. A.; Crich, D.; Fuchs, P. L.; Molander,
G. eds.; John Wiley & Sons, Ltd. DOI: 10.1002/047084289X.rc148.
1 Synthesis of the precursor polymer
1.1 An efficient route to the monomer
The desired monomer couples an aryl halide to a benzyilic anion (functionalities "A" and
"B", respectively, Scheme I) Our first synthesis of the monomer was performed in six steps as
shown in Scheme II. Even though it was a long synthesis, it was successful where other, simpler
approaches failed.Gorman/NCSU, "Direct Writing via Novel Aromatic Ladder Polymer Precursors"Page 3 of 17
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Gorman, C. B. Final Report for Grant "Direct Writing via Novel Aromatic Ladder Polymer Precursors", report, October 29, 2010; Raleigh, North Carolina. (https://digital.library.unt.edu/ark:/67531/metadc1013850/m1/3/: accessed April 18, 2024), University of North Texas Libraries, UNT Digital Library, https://digital.library.unt.edu; crediting UNT Libraries Government Documents Department.