journal article·2021-02Open access

Functionalized Tetrapodal Diazatriptycenes for Electrostatic Dipole Engineering in n‐Type Organic Thin Film Transistors

Valentina Rohnacher, Frank S. Benneckendorf, Maybritt Münch, Eric Sauter, Andika Asyuda, Marc‐Michael Barf, Jean‐Nicolas Tisserant, Sabina Hillebrandt, Frank Rominger, Daniel Jänsch, Jan Freudenberg, Wolfgang Kowalsky, Wolfram Jaegermann, Uwe H. F. Bunz, Annemarie Pucci, Michael Zharnikov, Klaus Müllen

Advanced Materials Technologies· Volume 6· Issue 2

Abstract

Abstract A diazatriptycene‐based tetrapodal scaffold with thiol anchors enforces a nearly upright orientation of functional groups, introduced to its quinoxaline subunit, with respect to the substrate upon formation of self‐assembled monolayers (SAMs). Substitution with electron‐withdrawing fluorine and cyano as well as electron‐rich dimethylamino substituents allows tuning of the molecular dipole and, consequently, of the work function of gold over a range of 1.0 eV (from 3.9 to 4.9 eV). The properties of the SAMs are comprehensively investigated by infrared reflection absorption spectroscopy, near edge X‐ray absorption fine structure spectroscopy, and X‐ray photoelectron spectroscopy. As prototypical examples for the high potential of the presented SAMs in devices, organic thin‐film transistors are fabricated.
Source: crossref · Quality: baseline

Research context

OpenAlex topics: Molecular Junctions and Nanostructures · Organic Electronics and Photovoltaics · Organic Light-Emitting Diodes Research

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Kirchhoff Institute for Physics Heidelberg University Im Neuenheimer Feld 227 Heidelberg 69120 Germany

InnovationLab Speyerer Straße 4 Heidelberg 69115 Germany

Organisch‐Chemisches Institut Ruprecht‐Karls‐Universität Heidelberg Im Neuenheimer Feld 270 Heidelberg 69120 Germany

Material Science Department Surface Science Division Technische Universität Darmstadt Otto‐Berndt‐Straße 3 Darmstadt 64287 Germany

Applied Physical Chemistry Heidelberg University Im Neuenheimer Feld 253 Heidelberg 69120 Germany

Institut für Hochfrequenztechnik Technische Universität Braunschweig Schleinitzstraße 22 Braunschweig 38106 Germany

Max‐Planck Institute for Polymer Research Ackermannweg 10 Mainz 55128 Germany

Funding

Bundesministerium für Bildung und Forschung · Deutsche Forschungsgemeinschaft

References (57)

Show source-provided references
1. 10.1039/C4RA04659E10.1039/C4RA04659E ↗
2. 10.1021/acsami.8b1542710.1021/acsami.8b15427 ↗
3. 10.1021/ar010084w10.1021/ar010084w ↗
4. 10.1002/anie.20070533910.1002/anie.200705339 ↗
5. 10.1021/ja900507c10.1021/ja900507c ↗
6. 10.1103/RevModPhys.65.59910.1103/RevModPhys.65.599 ↗
7. 10.1002/adma.20030609110.1002/adma.200306091 ↗
8. 10.1038/nphoton.2016.4310.1038/nphoton.2016.43 ↗
9. 10.1021/acsami.7b1278410.1021/acsami.7b12784 ↗
10. 10.1002/adfm.20090031510.1002/adfm.200900315 ↗
11. 10.1002/adma.20100150210.1002/adma.201001502 ↗
12. 10.1063/1.181020510.1063/1.1810205 ↗
13. 10.1038/nmat110510.1038/nmat1105 ↗
14. 10.1002/adfm.20080146610.1002/adfm.200801466 ↗
15. 10.1021/acs.langmuir.5b0231610.1021/acs.langmuir.5b02316 ↗
16. 10.1002/adfm.20150538610.1002/adfm.201505386 ↗
17. 10.1021/acs.langmuir.5b0276110.1021/acs.langmuir.5b02761 ↗
18. 10.1021/acs.chemrev.6b0006110.1021/acs.chemrev.6b00061 ↗
19. 10.1021/cr030078910.1021/cr0300789 ↗
20. 10.1021/acs.jpclett.8b0124210.1021/acs.jpclett.8b01242 ↗
21. 10.1002/adfm.20180446210.1002/adfm.201804462 ↗
22. 10.1002/adma.20040121610.1002/adma.200401216 ↗
23. 10.1021/acsami.9b1606210.1021/acsami.9b16062 ↗
24. 10.1002/asia.20190098910.1002/asia.201900989 ↗
25. 10.1021/jo990981210.1021/jo9909812 ↗
26. 10.1039/B515727G10.1039/B515727G ↗
27. 10.1002/chem.20160201910.1002/chem.201602019 ↗
28. 10.1039/c3cc42478b10.1039/c3cc42478b ↗
29. 10.1039/b823330f10.1039/b823330f ↗
30. 10.1021/jo501029t10.1021/jo501029t ↗
31. 10.1002/ange.20180036710.1002/ange.201800367 ↗
32. 10.1002/chem.20190361510.1002/chem.201903615 ↗
33. 10.1021/jacs.9b0095010.1021/jacs.9b00950 ↗
34. 10.1021/ja068218u10.1021/ja068218u ↗
35. 10.1039/C5NR04087F10.1039/C5NR04087F ↗
36. 10.1021/ja807923f10.1021/ja807923f ↗
37. 10.1021/cr950235710.1021/cr9502357 ↗
38. 10.1002/slct.20160045410.1002/slct.201600454 ↗
39. Stöhr J. · 2003
40. Richard G. · J. Phys. IV · 1993 · 03 · C7
41. 10.1016/0368-2048(88)85015-110.1016/0368-2048(88)85015-1 ↗
42. 10.1063/1.45750710.1063/1.457507 ↗
43. 10.1021/jp207887410.1021/jp2078874 ↗
44. 10.1016/j.elspec.2015.05.02210.1016/j.elspec.2015.05.022 ↗
45. 10.1016/j.elspec.2009.05.00810.1016/j.elspec.2009.05.008 ↗
46. 10.1002/adma.20150462910.1002/adma.201504629 ↗
47. 10.1021/am505768910.1021/am5057689 ↗
48. 10.1021/acs.jpcc.9b1015510.1021/acs.jpcc.9b10155 ↗
49. W.Theiss SCOUT—Software Package for Optical Spectroscopy WTheiss Hardware and Software Tucson AZ 85749 USA.
50. Moulder J. F. · 1992
51. 10.1021/la980831710.1021/la9808317 ↗
52. 10.1039/C9CP03306H10.1039/C9CP03306H ↗
53. 10.1016/S0079-6816(00)00024-110.1016/S0079-6816(00)00024-1 ↗
54. 10.1103/PhysRevB.48.260810.1103/PhysRevB.48.2608 ↗
55. 10.1021/acs.chemmater.5b0198210.1021/acs.chemmater.5b01982 ↗
56. 10.1038/ncomms1090810.1038/ncomms10908 ↗
57. 10.1063/1.240050710.1063/1.2400507 ↗