Soluble Diazaiptycenes: Materials for Solution-Processed Organic Electronics

Biegger, Philipp; Stolz, Sebastian; Intorp, Sebastian N.; Zhang, Yexiang; Engelhart, Jens U.; Röminger, Frank; Hardcastle, Kenneth I.; Lemmer, Uli; Qian, Xuhong; Hamburger, Manuel; Bunz, Uwe H. F.

doi:10.1021/jo502564w

Cited by 66 publications

(75 citation statements)

References 26 publications

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“…We demonstrated that triptycene‐carrying diazatetracenes are efficient emitters in organic light‐emitting diodes (OLEDs), increasing the diode's brightness by a factor of more than 200. The effect is likely due to the inhibition of crystallization . While for OLEDs this amorphization is critical, the same might be true for organic photovoltaic devices (OPVs).…”

Section: Introductionmentioning

confidence: 99%

“…6,13‐Bis((triisopropylsilyl)ethynyl)‐5,7,12,14‐tetraazapentacene (TAP; 2 ) forms crystalline films with excellent electron mobilities, however, the direct synthesis of TAP by using the diamine 1 in a condensation with simple ortho ‐quinones or dihalobenzenes (Pd catalyzed) remains challenging (Scheme ), and 2 is typically prepared via the intermediate 5 , followed by its oxidation into 6 and subsequent alkynylation. In contrast, the condensation of stable triptycene‐2,3‐dione with alkynylated diamines is efficient and leads to azaiptycenes in high yields (Scheme ) …”

Section: Introductionmentioning

confidence: 99%

“… Efficient synthesis of triptycene‐substituted azapentacene 9 through classical condensation with the stable triptycene‐2,3‐dione from Bunz et al …”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Triptycene‐Substituted Azapentacene and Azahexacene Derivatives

Biegger

Tverskoy

Röminger

et al. 2016

Chemistry A European J

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We describe the synthesis and characterization of novel iptycene-substituted azaacenes by using either a classic condensation route (diamine plus ortho-quinone) and/or a Pd-catalyzed coupling of an aromatic diamine with an aromatic dihalide. The attachment of an iptycene unit leads to a significant blueshift (15 nm) in the UV/Vis spectra of these azaacenes. The iptycene unit stabilizes a hexaazahexacene with a λ of 833 nm. By employing 5,6-diamino(benzothiadiazole) as a synthon for tetraaminobenzene, we could prepare the symmetrical bis-triptycene-substituted tetraazapentacene in high yields.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of Triptycene‐Substituted Azapentacene and Azahexacene Derivatives

Biegger

Tverskoy

Röminger

et al. 2016

Chemistry A European J

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“…6 The most frequently used reactions to construct such π-extended triptycenes are condensation reactions, e.g. of diketones with diamine moieties.…”

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confidence: 99%

“…, 7.19 (dd, J = 8.8, 2.5 Hz, 6H,10',3,6,14,17), 6.18 (s, 2H, bridgehead-H), 4.02 (s, 18H, OCH 3 ) ppm; 13 C NMR (151 MHz, C 2 D 2 Cl 4 ): δ 158.2 (C…”

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confidence: 99%

Synthesis of Triphenylene-Based Triptycenes via Suzuki–Miyaura Cross-Coupling and Subsequent Scholl Reaction

2015

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Controlling the Chromaticity of Small‐Molecule Light‐Emitting Electrochemical Cells Based on TIPS‐Pentacene

Weber

Adam

Tykwinski

et al. 2015

Adv Funct Materials

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5066 wileyonlinelibrary.com the most intriguing archetypal compounds. For instance, remarkable charge mobilities of up to 4.6 cm 2 V −1 s −1 for its solution-sheared thin fi lms applied in OFETs have been achieved. [ 8 ] Recently, the same authors have demonstrated that the control of the structural arrangement in fi lms boosts the fi eld-effect mobility to remarkable values of 11 cm 2 V −1 s −1 . [ 9 ] In addition, this molecule has recently emerged as a paradigm to study singlet fi ssion process in both solution and thin fi lms, owing to its triplet quantum yield formation exceeding values of 100%. [ 5,6,[10][11][12][13] Finally, the sharp red emission at around 650 nm and the moderate photoluminescence quantum yields (PLQYs) when dispersed in a thin fi lm with the electrontransporting host tris(quinoline-8-olato)-aluminum(III) (Alq 3 ) prompted Kafafi and Anthony groups to fabricate the fi rst OLEDs based on trialkylsilylethynyl-substitute pentacenes. [ 14,15 ] As the most remarkable result, the authors demonstrated that through a proper design of the molecular structure a near quantitative internal quantum effi ciency based on the PLQYs of the active layer is realized. [ 16 ] Encouraged by this excellent result, we decided to probe the performance of the archetypal TIPS-pentacene as an emitter in small molecule light-emitting electrochemical cells (SM-LECs).LECs have emerged as an interesting alternative to OLEDs due to the single-layer device architecture based on air-stable electrodes, the high power effi ciencies at very low operation voltages, and the low-cost manufacturing process on any 3D-shaped substrate. [17][18][19][20][21][22] These assets are possible due to the unique mechanism as the active layer comprises a blend of mobile ions and mostly one electroactive compound. [23][24][25][26][27] Up to date, the most representative materials for LECs have been mixtures of a light-emitting polymer, an ion conducting polymer, and an inorganic salt, as well as mixtures of ionic transition-metal complexes (iTMCs) and ionic liquids. [19][20][21] However, Edman and co-workers have recently demonstrated that the LEC concept can be easily expanded to small molecule (SM) materials. [ 28 ] This result represents a landmark toward future breakthroughs in the fi eld, especially if we take into account the very recent achievements in SM-based OLEDs that are considered as the new momentum heading into the third generation of this technology, [29][30][31][32][33] as well as SMs are considered as the third generation of materials for LECs, which is now in its early infancy. [ 28,34 ] Controlling the Chromaticity of Small-Molecule LightEmitting Electrochemical Cells Based on TIPS-Pentacene

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Soluble Diazaiptycenes: Materials for Solution-Processed Organic Electronics

Cited by 66 publications

References 26 publications

Synthesis of Triptycene‐Substituted Azapentacene and Azahexacene Derivatives

Synthesis of Triptycene‐Substituted Azapentacene and Azahexacene Derivatives

Synthesis of Triphenylene-Based Triptycenes via Suzuki–Miyaura Cross-Coupling and Subsequent Scholl Reaction

Controlling the Chromaticity of Small‐Molecule Light‐Emitting Electrochemical Cells Based on TIPS‐Pentacene

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