Design and synthesis of highly twisted phenanthroimidazole substituted blue-emitting truxene based fluorescent chromophores

Kaur, Banpreet; Moghe, Dhanashree; Kabra, Dinesh; Jacob, Josemon

doi:10.1039/c8nj04293d

Cited by 8 publications

(3 citation statements)

References 47 publications

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“…To investigate the electrochemical properties of triformyl triindolo‐truxenes, cyclic voltammetry was conducted in dichloromethane (Figure 5, data were summarized in Table 1). Triformyl triindolo‐truxenes showed lower HOMO and LUMO levels than those of pristine triindolo‐truxenes as a result of the incorporation of electron‐deficient formyl groups [23] . The HOMO levels, calculated from the first oxidation potential onsets, were lowered from −5.57 eV [7b] for 1 a to −5.74 eV for 1 b and −5.67 eV for 1 c .…”

Section: Resultsmentioning

confidence: 93%

“…Triformyl triindolo-truxenes showed lower HOMO and LUMO levels than those of pristine triindolo-truxenes as a result of the incorporation of electron-deficient formyl groups. [23] The HOMO levels, calculated from the first oxidation potential onsets, were lowered from À 5.57 eV [7b] for 1 a to À 5.74 eV for 1 b and À 5.67 eV for 1 c. The LUMO levels, determined from their first reduction potential onsets, were also lowered from À 2.08 eV [7b] for 1 a to approximate À 2.68 eV for 1 b and 1 c. Similar change tendency of HOMO and LUMO levels was observed in 2 a-2 c. The HOMO-LUMO gaps (E g cv ) of triformyl triindolo-truxenes were narrower than those of triindolo-truxenes, which were consistent with their red-shifted absorption onsets (Figure 3a and 3b) and narrower optical bandgaps (E g opt ).…”

Section: Electrochemical Propertiesmentioning

confidence: 99%

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C_3h‐symmetric and C_s‐symmetric Triformyl Triindolo‐Truxenes: Synthesis and Properties

Chen

Wang

et al. 2021

Asian J Org Chem

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C3h‐symmetric and Cs‐symmetric triformyl triindolo‐truxenes with different substitution positions of formyl groups were developed by two synthetic strategies. Direct formylation of triindolo‐truxene using Rieche formylation produced C3h‐symmetric and Cs‐symmetric triformyl triindolo‐truxenes in one‐pot. Four‐step synthesis starting from truxene gave a carbonyl‐modified C3h‐symmetric triformyl triindolo‐truxene. The optical and electrochemical properties of triformyl triindolo‐truxenes were modulated by changing the substitution positions of formyl groups and introducing carbonyl groups into molecules. The Cs‐symmetric triformyl triindolo‐truxenes exhibited red‐shifted absorption and emission, higher HOMO levels, and narrower HOMO‐LUMO gaps than those of C3h‐symmetric analogues. Furthermore, carbonyl‐modified C3h‐symmetric triformyl triindolo‐truxene showed the longest absorption and emission and narrowest HOMO‐LUMO gap among its analogues. The assembly of triformyl triindolo‐truxenes in single crystals and solution was investigated. This work provides valuable building blocks for constructing supramolecular architectures and adds new aspects of reactivity and structure‐property relationship of triindolo‐truxene.

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Section: Resultsmentioning

confidence: 93%

Section: Electrochemical Propertiesmentioning

confidence: 99%

C_3h‐symmetric and C_s‐symmetric Triformyl Triindolo‐Truxenes: Synthesis and Properties

Chen

Wang

et al. 2021

Asian J Org Chem

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“…Structures of some other interesting truxenes ( 55‐57 ) which have been recently synthesized by different research groups are shown in figure . These compounds display potential applications in solar cells as well as in coordination and organometallic chemistry …”

Section: Some Selected Recent Approaches Towards the Synthesis Of Trumentioning

confidence: 99%

Functionalized Truxene Scaffold: A Promising Advanced Organic Material for Digital Era

2019

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Truxene and its congeners due to its structural, thermal, and optoelectronic properties, has recently became important not only in biological systems but also in the field of material and environmental sciences. The remarkable scope and its applicability ranging from sensory materials to photocatalysts and fluorescent probes, forces the scientific community to think about the design and construction of architecturally simple yet much powerful novel functional materials possessing the truxene scaffold(s) in their structures. Herein, we have focused to assemble a series of ground‐breaking achievements in recent years of truxene‐based functional materials with special emphasis on their applicability in material sciences and technology. We hope that the present review will boost the current scenario of truxene and its various domains.

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Design, Synthesis and Selective Functionalization of a Rigid, Truxene Derived Pure Blue‐Emitting Chromophore

et al. 2020

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A novel, rigid, solution processable, blue‐emitting chromophore based on an extended core of truxene (ExT) was designed and synthesized. The core, ExT based on a fused cyclic trimer of indenofluorene, was found to be planar in nature and a potential precursor for blue emission. This could be selectively brominated under mild conditions to generate a tribromo derivative which underwent ready Suzuki coupling to generate a trisubstituted pyrene derivative, ExT‐P. This coupling alters the kinetics of the excited state considerably as evident from transient absorption spectroscopy, showing faster singlet state decay and less triplet state formation in the case of the pyrene coupled ExT‐P (∼1.6 ns) compared to ExT (∼17 ns). The ExT‐P shows emission maxima at 441 nm and 442 nm in THF solution and film, respectively, with high PLQY value of 0.97. The negligible bathochromic shift in the solid‐state emission and narrow FWHM suggests practically no aggregation and pure blue emission in the target molecule due to bulky and rigid core.

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Design and synthesis of highly twisted phenanthroimidazole substituted blue-emitting truxene based fluorescent chromophores

Abstract: Highly twisted truxene–phenanthroimidazole conjugates have been designed to obtain blue chromophores. The materials show good quantum yields of up to 0.83 and predominant radiative pathways.

Cited by 8 publications

References 47 publications

C_3h‐symmetric and C_s‐symmetric Triformyl Triindolo‐Truxenes: Synthesis and Properties

C_3h‐symmetric and C_s‐symmetric Triformyl Triindolo‐Truxenes: Synthesis and Properties

Functionalized Truxene Scaffold: A Promising Advanced Organic Material for Digital Era

Design, Synthesis and Selective Functionalization of a Rigid, Truxene Derived Pure Blue‐Emitting Chromophore

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Design and synthesis of highly twisted phenanthroimidazole substituted blue-emitting truxene based fluorescent chromophores

Abstract: Highly twisted truxene–phenanthroimidazole conjugates have been designed to obtain blue chromophores. The materials show good quantum yields of up to 0.83 and predominant radiative pathways.

Cited by 8 publications

References 47 publications

C3h‐symmetric and Cs‐symmetric Triformyl Triindolo‐Truxenes: Synthesis and Properties

C3h‐symmetric and Cs‐symmetric Triformyl Triindolo‐Truxenes: Synthesis and Properties

Functionalized Truxene Scaffold: A Promising Advanced Organic Material for Digital Era

Design, Synthesis and Selective Functionalization of a Rigid, Truxene Derived Pure Blue‐Emitting Chromophore

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Product

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C_3h‐symmetric and C_s‐symmetric Triformyl Triindolo‐Truxenes: Synthesis and Properties

C_3h‐symmetric and C_s‐symmetric Triformyl Triindolo‐Truxenes: Synthesis and Properties