Real-Time Optical and Electronic Sensing with a β-Amino Enone Linked, Triazine-Containing 2D Covalent Organic Framework

Kulkarni, Ranjit; Noda, Yu; Barange, Deepak K.; Kochergin, Yaroslav S.; Balcarova, Barbora; Lyu, Pengbo; Nachtigall, Petr; Bojdys, Michael J.

doi:10.26434/chemrxiv.7973804.v1

Cited by 12 publications

(17 citation statements)

References 39 publications

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“…Recently, we showed, that triazine-containing COFs, made by the same principle, can be also exploited as acid/base chemosensors, thus, highlighting the significance of our approach in view of making multifunctional smart materials. 24 Herein, we choose four previously reported SNP systems as reference: SNP-NDT1, SNP-NDT2, SNP-BTT1 and SNP-BTT2 that consist of electron-donating thiophene-based naphthodithiophene (NDT) and benzotrithiophene (BTT) moieties, and electron-withdrawing 1,3,5-triazine (Tz) and tris-phenyltriazine moieties (Scheme 1). 18 In addition, we expand the family of SNPs by three networks, two of which contain a benzodithiophene (BDT) moiety -SNP-BDT1 and SNP-BDT2.…”

Section: Introductionmentioning

confidence: 99%

Sulfur- and Nitrogen-Containing Porous Donor–Acceptor Polymers as Real-Time Optical and Chemical Sensors

et al. 2019

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Real-Time Optical and Chemical Sensors. ChemRxiv. Preprint.Fully aromatic, organic polymers have the advantage of being composed from light, abundant elements, and are hailed as candidates in electronic and optical devices "beyond silicon", yet, applications that make use of their π-conjugated backbone and optical bandgap are lacking outside of heterogeneous catalysis. Herein, we use a series of sulfur-and nitrogen-containing porous polymers (SNPs) as real-time optical and electronic sensors reversibly triggered and re-set by acid and ammonia vapors. Our SNPs incorporate donor-acceptor and donor-donor motifs in extended networks and enable us to study the changes in bulk conductivity, optical bandgap, and fluorescence life-times as a function of π-electron de-/localization in the pristine and protonated states. Interestingly, we find that protonated donor-acceptor polymers show a decrease of the optical bandgap by 0.42 eV to 0.76 eV and longer fluorescence life-times. In contrast, protonation of a donor-donor polymer does not affect its bandgap; however, it leads to an increase of electrical conductivity by up to 25-fold and shorter fluorescence life-times. The design strategies highlighted in this study open new avenues towards useful chemical switches and sensors based on modular purely organic materials. File list (4) download file view on ChemRxiv 20190929_Manuscript_CLEAN.docx (1.67 MiB) download file view on ChemRxiv 20190929_SI_CLEAN.docx (16.08 MiB) download file view on ChemRxiv 20190929_Manuscript_CLEAN.pdf (1.23 MiB) download file view on ChemRxiv Video 1-YAR SNP-NDT1.mp4 (3.71 MiB)

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Section: Introductionmentioning

confidence: 99%

Sulfur- and Nitrogen-Containing Porous Donor–Acceptor Polymers as Real-Time Optical and Chemical Sensors

et al. 2019

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“…Previous DFT calculations confirm that the Lewis basic N-atoms of the triazine moieties are the preferred site of protonation. 24 This rapid and fully-reversible detection of HCl vapors at low concentrations makes SNPs suitable candidates for naked-eye sensors. Moreover, we monitored the response of SNP-NDT1…”

Section: Resultsmentioning

confidence: 99%

Sulfur- and Nitrogen-Containing Porous Donor-Acceptor Polymers as Real-Time Optical and Chemical Sensors

Kochergin¹,

Noda²,

Kulkarni³

et al. 2019

Preprint

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Fully aromatic, organic polymers have the advantage of being composed from light, abundant elements, and are hailed as candidates in electronic and optical devices “beyond silicon”, yet, applications that make use of their π-conjugated backbone and optical bandgap are lacking outside of heterogeneous catalysis. Herein, we use a series of sulfur- and nitrogen-containing porous polymers (SNPs) as real-time optical and electronic sensors reversibly triggered and re-set by acid and ammonia vapors. Our SNPs incorporate donor-acceptor and donor-donor motifs in extended networks and enable us to study the changes in bulk conductivity, optical bandgap, and fluorescence life-times as a function of π-electron de-/localization in the pristine and protonated states. Interestingly, we find that protonated donor-acceptor polymers show a decrease of the optical bandgap by 0.42 eV to 0.76 eV and longer fluorescence life-times. In contrast, protonation of a donor-donor polymer does not affect its bandgap; however, it leads to an increase of electrical conductivity by up to 25-fold and shorter fluorescence life-times. The design strategies highlighted in this study open new avenues towards useful chemical switches and sensors based on modular purely organic materials.

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“…Covalent organic frameworks (COFs) are a growing class of crystalline porous materials that have garnered extensive interest for their auspicious employments in numerous applications, including gas adsorption and separation, [1][2][3][4][5] heterogeneous catalysis, [6][7][8][9][10] energy storage, [11][12][13] chemical sensing, [14][15][16] and so on. [17][18][19][20] One of the unique characteristics of COFs is the atomic precision with which molecular building blocks are integrated into two-dimensional (2D) or three-dimensional (3D) extended architectures via diverse covalent bond linkages.…”

Section: Introductionmentioning

confidence: 99%

Tunable Cage-Based Three-Dimensional Covalent Organic Frameworks

Wang

et al. 2022

CCS Chem

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It is highly challenging to construct three-dimensional (3D) crystalline covalent organic frameworks (COFs) with flexible building blocks and further explore their tunable or adaptive characteristics due to crystallization and structure determination difficulties. Herein, we constructed three crystalline isostructural 3D-OC-COFs based on a newly synthesized flexible organic cage (6NH 2 -OC•4HCl) through a novel "in-situ acid-base neutralization strategy". Interestingly, network conformations could be fine-tuned by rationally introducing different substituents into the starting dialdehydes during the assembly process, resulting in one expanded structure (3D-OC-COF-H) and two different contracted structures (3D-OC-COF-OH and 3D-OC-COF-Cl), which mainly ascribed to the hinge-like motions of organic cage building blocks. By virtue of the unique pore environments and different functional groups, we further employed these COFs for CO 2 capture, of which 3D-OC-COF-OH exhibited superior CO 2 /CH 4 separation performance. This study not only demonstrates a new strategy for constructing 3D cage-based COFs, but also identifies a novel factor that affects flexible building blocks for realizing structural diversity.

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Real-Time Optical and Electronic Sensing with a β-Amino Enone Linked, Triazine-Containing 2D Covalent Organic Framework

Cited by 12 publications

References 39 publications

Sulfur- and Nitrogen-Containing Porous Donor–Acceptor Polymers as Real-Time Optical and Chemical Sensors

Sulfur- and Nitrogen-Containing Porous Donor–Acceptor Polymers as Real-Time Optical and Chemical Sensors

Sulfur- and Nitrogen-Containing Porous Donor-Acceptor Polymers as Real-Time Optical and Chemical Sensors

Tunable Cage-Based Three-Dimensional Covalent Organic Frameworks

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