Abstract
AbstractAzaacenes have been known for a very long time, either as N,N′‐dihydro compounds or in their oxidized form as 4 n+2π systems, but only recently have processable and charcterizable derivatives been sought. In the last three years synthetic routes to large N‐heteroacenes have been developed. In particular, the Pd‐catalyzed coupling of aromatic diamines with activated aromatic dihalogenides has enabled simple access to numerous new azaacenes. Since 2010, azapentacene and stabile oligoazahexacene have been synthesized, as well as a symmetrical tetraazapentacene, which acts as an excellent electron‐transport material for thin‐film transistors.
References
79
Referenced
460
10.1063/1.1704874
10.1002/ange.200604045
10.1002/anie.200604045
10.1021/cr050966z
10.1021/ja0476258
10.1021/ol050872b
10.1021/ja809045s
10.1351/PAC-CON-09-09-17
10.1002/chem.200900990
10.1055/s-0031-1290323
10.1039/c1ob05454f
10.1002/cber.19290621113
10.1002/cber.19300631109
10.1002/cber.19310640507
10.1002/jlac.19013190302
10.1002/cber.189002302190
10.1002/cber.18950280170
10.1002/bbpc.19670710922
10.1021/jo01349a058
10.1021/ja036466
10.1021/jo900684c
10.1002/chem.200900160
10.1021/ol203404q
10.1002/cphc.200600266
10.1021/ja067087u
10.1039/c2jm33039c
10.1002/adma.201103759
10.1021/jp206617e
10.1039/c1cp20391f
10.1038/ncomms1088
10.1002/chem.201103227
{'key': 'e_1_2_12_36_2', 'first-page': '1983', 'author': 'Appleton A. L.', 'year': '2011', 'journal-title': 'Synlett'}
/ Synlett by Appleton A. L. (2011)10.1021/ol301841h
10.1002/chem.200802148
10.1002/asia.200900373
10.1021/ja800311a
10.1021/ja072521t
10.1039/C0SC00331J
10.1002/ange.201007654
10.1002/anie.201007654
10.1002/ange.201103676
10.1002/anie.201103676
10.1021/ja051798v
- See Ref. [13].
10.1021/ol203334u
10.1002/adma.201004325
10.1002/chem.200900324
10.1021/ja0162459
10.1021/ja107046s
10.1021/ol2008999
10.1021/ol301854z
10.1002/chem.201103350
10.1021/am9004418
10.1039/c2nj21033a
10.1039/c2cc31613g
{'key': 'e_1_2_12_60_2', 'first-page': '280', 'author': 'Engelhardt V.', 'year': '2011', 'journal-title': 'Synlett'}
/ Synlett by Engelhardt V. (2011)10.1021/ol902366y
10.1002/anie.201204863
10.1002/ange.201204863
10.1039/c2cc32048g
10.1021/ja0553147
10.1021/ol2030839
10.1021/ol201717d
10.1021/ar900218d
10.1002/chem.201103158
10.1021/cr100380z
10.1021/la203623s
- See Ref. [23b].
10.1021/ol0167356
- B. D. Lindner F. Paulus H. Reiss U. H. F. Bunz unpublished results.
10.1039/c1jm13153b
Dates
Type | When |
---|---|
Created | 12 years, 6 months ago (Feb. 18, 2013, 8:47 p.m.) |
Deposited | 1 year, 10 months ago (Oct. 16, 2023, 8:30 a.m.) |
Indexed | 4 weeks, 2 days ago (Aug. 5, 2025, 8:19 a.m.) |
Issued | 12 years, 6 months ago (Feb. 18, 2013) |
Published | 12 years, 6 months ago (Feb. 18, 2013) |
Published Online | 12 years, 6 months ago (Feb. 18, 2013) |
Published Print | 12 years, 5 months ago (April 2, 2013) |
@article{Bunz_2013, title={Large N‐Heteroacenes: New Tricks for Very Old Dogs?}, volume={52}, ISSN={1521-3773}, url={http://dx.doi.org/10.1002/anie.201209479}, DOI={10.1002/anie.201209479}, number={14}, journal={Angewandte Chemie International Edition}, publisher={Wiley}, author={Bunz, Uwe H. F. and Engelhart, Jens U. and Lindner, Benjamin D. and Schaffroth, Manuel}, year={2013}, month=feb, pages={3810–3821} }