A Stable Hexaazaoctacene Cruciform σ‐Dimer
Source abstract
Abstract
Abstract Buchwald‐Hartwig coupling of a triisopropylsilyl (TIPS)‐ethynylated dibromo‐N,N'‐dihydrotetraazapentacene with 1,4‐bis(TIPS‐ethynyl)‐2,3‐diaminonaphthalene furnishes a dihydrohexaazaoctacene. Its oxidation with MnO2 results in a 7,7'‐bi(hexaazaoctacenyl). In addition to eight TIPS‐ethynyl groups, the bioctacene motif protects the azaoctacene subunits. The biazaoctacenyl displays a τ1/2 of > 5 d in dilute solution under ambient conditions. In the crystalline state it is persistent for > 10 months.
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Research context
OpenAlex topics: Synthesis and Properties of Aromatic Compounds · Supramolecular Chemistry and Complexes · Luminescence and Fluorescent Materials
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Organisch‐Chemisches Institut Ruprecht‐Karls‐Universität Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Germany
Interdisziplinäres Zentrum für Wissenschaftliches Rechnen Universität Heidelberg Im Neuenheimer Feld 205A 69120 Heidelberg Germany
Physikalisch‐Chemisches Institut Universität Heidelberg Im Neuenheimer Feld 253 69120 Heidelberg Germany
Centre for Advanced Materials (CAM) Ruprecht‐Karls‐Universität Heidelberg Im Neuenheimer Feld 225 69120 Heidelberg Germany
Funding
Deutsche Forschungsgemeinschaft
References (60)
Show source-provided references
1. 10.1002/anie.20060404510.1002/anie.200604045 ↗
2. 10.1002/chem.20200311210.1002/chem.202003112 ↗
3. 10.1021/jp984066g10.1021/jp984066g ↗
4. 10.1021/jacs.6b1321210.1021/jacs.6b13212 ↗
5. 10.1016/0040-4020(80)80116-510.1016/0040-4020(80)80116-5 ↗
6. 10.1021/ja306056x10.1021/ja306056x ↗
7. 10.1002/anie.20180204010.1002/anie.201802040 ↗
8. 10.1021/ja063823i10.1021/ja063823i ↗
9. 10.1021/jacs.7b0519210.1021/jacs.7b05192 ↗
10. 10.1002/anie.20180219710.1002/anie.201802197 ↗
11. 10.1021/acsnano.9b0845610.1021/acsnano.9b08456 ↗
12. 10.1021/ol100178s10.1021/ol100178s ↗
13. 10.1021/ja051798v10.1021/ja051798v ↗
14. 10.1002/anie.20080334510.1002/anie.200803345 ↗
15. 10.1021/ol101158y10.1021/ol101158y ↗
16. 10.1002/anie.20110267110.1002/anie.201102671 ↗
17. 10.1021/ja016245910.1021/ja0162459 ↗
18. 10.1021/acs.accounts.9b0016010.1021/acs.accounts.9b00160 ↗
19. 10.1021/acs.accounts.5b0011810.1021/acs.accounts.5b00118 ↗
20. 10.1021/acsami.5b0011310.1021/acsami.5b00113 ↗
21. 10.1002/chem.20150051810.1002/chem.201500518 ↗
22. 10.1002/chem.20150501810.1002/chem.201505018 ↗
23. 10.1021/ol301854z10.1021/ol301854z ↗
24. 10.1021/ja509723q10.1021/ja509723q ↗
25. 10.1002/chem.20170410310.1002/chem.201704103 ↗
26. 10.1002/chem.20180107910.1002/chem.201801079 ↗
27. 10.1002/chem.20180311810.1002/chem.201803118 ↗
28. 10.1002/anie.20190961410.1002/anie.201909614 ↗
29. 10.1039/C9TC04843J10.1039/C9TC04843J ↗
30. 10.1002/chem.20200238210.1002/chem.202002382 ↗
31. 10.1002/chem.20190200210.1002/chem.201902002 ↗
32. 10.1002/anie.20141197210.1002/anie.201411972 ↗
33. 10.1002/asia.20150127610.1002/asia.201501276 ↗
34. 10.1021/acs.chemmater.7b0131810.1021/acs.chemmater.7b01318 ↗
35. 10.1039/C7CC03898D10.1039/C7CC03898D ↗
36. 10.1021/ol301841h10.1021/ol301841h ↗
37. 10.1039/c3cc48742c10.1039/c3cc48742c ↗
38. 10.1021/acs.orglett.6b0233210.1021/acs.orglett.6b02332 ↗
39. 10.1055/s-0034-137996510.1055/s-0034-1379965 ↗
40. 10.1039/C9QM00656G10.1039/C9QM00656G ↗
41. 10.1002/chem.20090267510.1002/chem.200902675 ↗
42. 10.1080/10406638.2019.162213410.1080/10406638.2019.1622134 ↗
43. 10.1021/jp902045410.1021/jp9020454 ↗
44. 10.1016/0009-2614(86)80072-010.1016/0009-2614(86)80072-0 ↗
45. 10.1002/anie.19850508110.1002/anie.198505081 ↗
46. 10.1016/0301-0104(94)89021-810.1016/0301-0104(94)89021-8 ↗
47. 10.1246/cl.20090910.1246/cl.200909 ↗
48. 10.1021/jo201659q10.1021/jo201659q ↗
49. 10.1002/adfm.20150153710.1002/adfm.201501537 ↗
50. 10.1002/anie.20150710410.1002/anie.201507104 ↗
51. 10.1002/anie.20080049710.1002/anie.200800497 ↗
52. 10.1002/anie.20211279410.1002/anie.202112794 ↗
53. 10.1039/C7CC09949E10.1039/C7CC09949E ↗
54. M. J.Frisch G. W.Trucks H. B.Schlegel G. E.Scuseria M. A.Robb J. R.Cheeseman G.Scalmani V.Barone G. A.Petersson H.Nakatsuji X.Li M.Caricato A. V.Marenich J.Bloino B. G.Janesko R.Gomperts B.Mennucci H. P.Hratchian J. V.Ortiz A. F.Izmaylov J. L.Sonnenberg D.Williams‐Young F.Ding F.Lipparini F.Egidi J.Goings B.Peng A.Petrone T.Henderson D.Ranasinghe Gaussian 16 Revision B.01 Gaussian Inc. Wallingford CT2016.
55. 10.1021/cr03008810.1021/cr030088 ↗
56. 10.1021/jp003442610.1021/jp0034426 ↗
57. 10.1021/cr030090110.1021/cr0300901 ↗
58. 10.1002/anie.20180572810.1002/anie.201805728 ↗
59. 10.1002/adma.20100455410.1002/adma.201004554 ↗
60. 10.1039/D0SC03744C10.1039/D0SC03744C ↗