Iptycene-Containing Azaacenes with Tunable Luminescence

Schleper, A. Lennart; Voll, Constantin-Christian A.; Engelhart, Jens U.; Swager, Timothy M.

doi:10.1055/s-0036-1589503

Cited by 8 publications

(6 citation statements)

References 33 publications

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“…For the synthesis of QPP derivatives with larger substituents, two different approaches were used (Scheme 1). First, the previously reported QPP-Br 24 was reacted with 3-benzothiophenyl boronic pinacol ester via the Suzuki-Miyaura cross-coupling reaction (Pd 2 (dba) 3 /P(o-tol) 3 /K 3 PO 4 in H 2 O/toluene/1,4-dioxane mixture at 60°C) 25 to give QPP-BTh in 14% yield. After ending the reaction, the solution contained mainly starting material along with some traces of one-fold coupled and one-fold dehydrobrominated product, which were not further purified.…”

Section: Synthesismentioning

confidence: 99%

Triptycene End-Capped Quinoxalinophenanthrophenazines with Aromatic Substituents – Synthesis, Characterization, and Single-Crystal Structure Analysis

et al. 2019

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In a previous study, we found that one-fold triptycene endcapped quinoxalinophenanthrophenazines (QPPs) arrange in crystals preferably in a coplanar fashion providing high overlap of the π-planes. Thus, resulting in high calculated charge transfer integrals. Most interestingly, this motif was observed for a variety of QPPs derivatives, independently of the nature of their peripheral substituents, e.g. bromide, methoxy, cyano, or triisopropylsilylethynyl groups, and of the crystallization conditions. Here, we describe the synthesis of another small series of three QPPs containing different aromatic substituents at the same position to get an insight, whether these aromatic substituents disturb the otherwise preferred π stacking of the QPP planes. d Intensity ratio between the first and second emission peak.A solution of diamine 1b (14.0 mg, 36.5 µmol) and diketone 2 23 (15.2 mg, 24.4 µmol) in chloroform (1.4 mL) and glacial acetic acid (0.07 mL) was stirred at 70°C under an

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Section: Synthesismentioning

confidence: 99%

Triptycene End-Capped Quinoxalinophenanthrophenazines with Aromatic Substituents – Synthesis, Characterization, and Single-Crystal Structure Analysis

et al. 2019

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“…The result shows that compound 1 has characteristic light absorption peak at 425 nm and fluorescence emission at 610 nm (excited at 408 nm), with a large stokes shift about 202 nm. The large stokes shift of compound 1 indicates that the azaacene‐bridged pentiptycene derivatives are potential compounds for optoelectronics, energy devices and biomedicine [11] …”

Section: Methodsmentioning

confidence: 99%

Ultrastable Anion Catechol Frameworks (ACFs) of Pentiptycene‐based Quad(catechol) Through Decavalent Hydrogen Bond

2022

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Anion coordination are silimar with metal coordination to direct the formation of ordered structures from samll building blocks through hydrogen bonds. However, the diversity and stablity of the reported anion coordinaion frameworks (ACFs) are limited. Herein, we designed and synthesized a new shape‐persistent catechol ligand, azazcene‐bridged pentiptycene with four catechol moieties, compound 1. The compound 1 with four catechol moieties as hydrogen bond donors and four nitrogen atoms as hydrogen bond acceptors will form more hydrogen bonds with anion ions or compound 1 itself to boost the development of anion catechol frameworks (ACFs). The obtained crystalline ACF possesses staggered hexagonal pores through decavalent hydrogen bond and exhibits excellent thermal and water stability in harsh conditions.

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“…37,38 As 4 is symmetrical, it is not possible to address the two halide groups individually during Suzuki coupling of the acceptor or donor moieties. 39 We first introduce the donor moiety to give compounds (5)(6)(7)(8), and then the acceptor moiety to give the target hot exciplex molecules (see Figure 2 and Experimentals in the Supplementary Information).…”

Section: Synthesismentioning

confidence: 99%

Hot Exciplexes in U-Shaped TADF Molecules with Emission from Locally Excited States

Schleper¹,

Goushi²,

Bannwarth³

et al. 2021

Preprint

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Rapid reverse intersystem crossing and high color purity are vital characteristics of emitters with thermally activated delayed fluorescence in opto-electronic devices. We present a new approach, called “hot exciplexes” that enables access to both attributes at the same time. Hot exciplexes are produced by coupling facing donor and acceptor moieties to an anthracene bridge, yielding an exciplex with large T1 to T2 spacing. The hot exciplex model is investigated using optical spec-troscopy and quantum chemical simulations. Reverse intersystem crossing is found to occur preferentially from the T3 to the S1 state within only a few nanoseconds. Application and practi-cality of the model are shown by fabrication of organic light-emitting diodes with up to 32 % hot exciplex contribution and low efficiency roll-off.

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Iptycene-Containing Azaacenes with Tunable Luminescence

Cited by 8 publications

References 33 publications

Triptycene End-Capped Quinoxalinophenanthrophenazines with Aromatic Substituents – Synthesis, Characterization, and Single-Crystal Structure Analysis

Triptycene End-Capped Quinoxalinophenanthrophenazines with Aromatic Substituents – Synthesis, Characterization, and Single-Crystal Structure Analysis

Ultrastable Anion Catechol Frameworks (ACFs) of Pentiptycene‐based Quad(catechol) Through Decavalent Hydrogen Bond

Hot Exciplexes in U-Shaped TADF Molecules with Emission from Locally Excited States

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