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Year 2024, Volume: 20 Issue: 3, 100 - 105, 30.09.2024
https://doi.org/10.18466/cbayarfbe.1516889

Abstract

References

  • [1]. Zhao, Z, Lam, JWY, Tang, BZ. 2012. Tetraphenylethene: a versatile AIE building block for the construction of efficient luminescent materials for organic light emitting diodes. J Mater Chem; 22:23726-40.
  • [2]. Huang, J, Yang, X, Li, X, Chen, P, Tang, R, Li, F, Lu, P, Ma, Y, Wang, L, Qin, J, Li, Q, Li, Z. 2012. Bipolar AIE-active luminogens comprised of an oxadiazole core and terminal TPE moieties as a new type of host for doped electroluminescence. Chem Commun; 48: 9586-8.
  • [3]. Martinez-Manez, R, Sancenon, F. 2003. Fluorogenic and chromogenic chemosensors and reagents for anions. Chem. Rev; 103(11): 4419-4476.
  • [4]. Wang, M, Zhang, G, Zhang, D, Zhu, D, Tang, BZ. 2010. Fluorescent bio/chemosensors based on silole and tetraphenylethene luminogens with aggregation-induced emission feature. J. Mater. Chem; 20: 1858.
  • [5]. Yang, Y, Zhao, Q, Feng, W, Li, F. 2013. Luminescent chemodosimeters for bioimaging. Chem. Rev; 113: 192.
  • [6]. Zhang, Q, Yu, P, Fan, Y, Sun, C, He, H, Liu, X, Lu, L, Zhao, M, Zhang, H, Zhang, F. 2020. Bright and stable NIR-II J-aggregated AIE dibodipy-based fluorescent probe for dynamic in vivo bioimaging. Angew. Chem., Int. Ed.; 60: 3967.
  • [7]. Shimizu, M, Takeda, Y, Higashi, M, Hiyama, T. 2009. 1,4-Bis(alkenyl)-2,5-dipiperidinobenzenes: minimal fluorophores exhibiting highly efficient emission in the solid state. Angew Chem Int Ed; 48: 3653-6.
  • [8] Xue, P, Sun, J, Chen, P, Gong, P, Yao, B, Zhang, Z, Qian, C, Lu, R. 2015. Strong solid emission and mechanofluorochromism of carbazole-based terephthalate derivatives adjusted by alkyl chains. J Mater Chem C; 3: 4086-92.
  • [9]. Yuan, WZ, Lu, P, Chen, S, Lam, JW, Wang, Z, Liu, Y, Kwok, HS, Ma, Y, Tang, BZ. 2010. Changing the behavior of chromophores from aggregation-caused quenching to aggregation-induced emission: development of highly efficient light emitters in the solid state. Adv Mater; 22: 2159-63.
  • [10]. Domaille, DW, Que, EL, Chang, CJ. 2008. Synthetic fluorescent sensors for studying the cell biology of metals. Nature Chemical Biology; 4: 168–175.
  • [11]. Hong, YN, Lam, JWY, Tang, BZ. 2011. Aggregation-induced emission. Chem. Soc. Rev; 40: 5361–5388.
  • [12]. Hong, YN, Lam, JWY, Tang, BZ. 2009. Aggregation-induced emission: phenomenon, mechanism and applications. Chem. Commun; 4332-4353.
  • [13]. Kwok, RTK, Leung, CWT, Lam, JWY, Tang, BZ. 2015. Chem. Soc. Rev; 44: 4228–4238.
  • [14]. Mei, J, Hong, Y, Lam, JWY, Qin, A, Tang, Y, Tang, BZ. 2014. Aggregation-Induced Emission: The Whole Is More Brilliant than the Parts. Adv. Mater; 26: 5429–5479.
  • [15]. Luo, J, Xie, Z, Lam, JWY, Cheng, L, Chen, H, Qiu, C, Kwok, HS, Zhan, X, Liu, Y, Zhu, D, Tang, BZ. 2001. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem. Commun; 1740–1741.
  • [16]. Kumbhar, HS, Shankarling, GS. 2015. Aggregation induced emission (AIE) active β-ketoiminate boron complexes: synthesis, photophysical and electrochemical properties. Dyes Pigments; 122: 85-93.
  • [17]. Kumar, M, Vij, V, Bhalla, V. 2012. Vapor-phase detection of trinitrotoluene by AIEE active hetero-oligophenylene-based carbazole derivatives. Langmuir; 28: 12417-21.
  • [18]. Shi, C, Guo, Z, Yan, Y, Zhu, S, Xie, Y, Zhao, YS, Zhu, W, Tian, H. 2013. Self-assembly solid-state enhanced red emission of quinolinemalononitrile: optical waveguides and stimuli response. ACS Appl. Mater. Interfaces; 5(1): 192-8.
  • [19]. Gu, X, Yao, J, Zhang, G, Zhang, C, Yan, Y, Zhao, Y, Zhang, D. 2013. New electron-donor/acceptor-substituted tetraphenylethylenes: aggregation-induced emission with tunable emission color and optical-waveguide behavior. Chem Asian J; 8(10): 2362-9.
  • [20]. Xu, F, Wang, H, Du, X, Wang, W, Wang, DE, Chen, S, Han, X, Li, N, Yuan, MS, Wang, J. 2016. Structure, property and mechanism study of fluorenone-based AIE dyes. Dyes and Pigments; 129: 121-128.
  • [21]. Du, X, Su, H, Zhao, L, Xing, X, Wang, B, Qiu, D, Wang, J, Yuan, MS. 2021. AIE-based donor–acceptor–donor fluorenone compound as multi-functional luminescence materials. Mater. Chem. Front; 5: 7508-7517.
  • [22]. Shaya, J, Corridon, PR, Al-Omari, B, Aoudi, A, Shunnar, A, Mohideen, MIH, Qurashi, A, Michel, BY, Burger, A. 2022. Design, photophysical properties, and applications of fluorene-based fluorophores in two-photon fluorescence bioimaging: A review. Journal of Photochemistry and Photobiology C: Photochemistry Reviews; 52, 100529.
  • [23]. Abbel, R, Schenning, APHJ, Meijer, EW. 2009. Fluorene-based materials and their supramolecular properties. J. Polym. Sci. Part A: Polym. Chem; 47: 4215–4233.
  • [24]. Moura, GLC, Simas, AM. 2010. Two-photon absorption by fluorene derivatives: systematic molecular design. J. Phys. Chem. C; 114(13): 6106–6116.
  • [25]. Kurdyukova, IV, Ishchenko AA. 2012. Organic dyes based on fluorene and its derivatives. Russ. Chem. Rev; 81: 258–290.
  • [26]. Ogawa, K. 2014. Two-photon absorbing molecules as potential materials for 3D optical memory. Appl. Sci; 4 (1): 1–18.
  • [27]. Lin, Y, Chen, Y, Ye, TL, Chen, ZK, Dai, YF, Ma, DG. 2012. Oligofluorene-based push–pull type functional materials for blue light-emitting diodes, J. Photochem. Photobiol. A: Chem; 230(1): 55-64.
  • [28]. Lim, K, Kim, C, Song, J, Yu, T, Lim, W, Song, K, Wang, P, Zu, N, Ko, J. 2011. Enhancing the performance of organic dye-sensitized solar cells via a slight structure modification. J. Phys. Chem. C; 115: 22640–22646.
  • [29]. Erdoğan, M, Horoz, S. 2021. Synthesis and characterization of a triphenylamine-dibenzosuberenone-based conjugated organic material and an investigation of its photovoltaic properties. Journal of Chemical Research; 45(1-2): 207-212.
  • [30]. Erdoğan, M, Orhan, Z, Daş, E. 2022. Synthesis of electron-rich thiophene triphenylamine based organic material for photodiode applications. Optical Materials; 128:12446.
  • [31]. Chen, ZQ, Chen, T, Liu, JX, Zhang, GF, Li, C, Gong, WL, Xiong ZJ, Xie, NH, Tang, BZ, Zhu, MQ. 2015. Geminal cross-coupling of 1, 1-dibromoolefins facilitating multiple topological π-conjugated tetraarylethenes. Macromolecules; 48(21): 7823-7835.
  • [32]. Yildirim-Sarikaya, S, Ardic-Alidagi, H, Cetindere, S. 2023. Novel BODIPY‑Fluorene‑Fullerene and BODIPY‑Fluorene‑BODIPY Conjugates: Synthesis, Characterization, Photophysical and Photochemical Properties. Journal of Fluorescence; 33: 297–304.
  • [33]. Tan, S, Yin, Y, Chen, W, Chen, Z, Tian, W, Pu, S. 2020. Carbazole-based highly solid-state emissive fluorene derivatives with various mechanochromic fluorescence characteristics. Dyes and Pigments; 177: 108302.
  • [34]. Chen, Z, Liang, J, Han, X, Yin, J, Yu, GA, Liu, SH. 2015. Fluorene-based novel highly emissive fluorescent molecules with aggregate fluorescence change or aggregation-induced emission enhancement characteristics. Dyes and Pigments; 112: 59-66.
  • [35]. Gouthaman, S, Jayaraj, A, Sugunalakshmi, M, Sivaraman, G, Swamy, PCA. 2022. Supramolecular self-assembly mediated aggregation-induced emission of fluorene-derived cyanostilbenes: multifunctional probes for live cell-imaging. J. Mater. Chem. B; 10: 2238.
  • [36]. Zhou, X, Li, H, Chi, Z, Zhang, X, Zhang, J, Xu, B, Zhang, Y, Liu, S, Xu, J. 2012. Piezofluorochromism and morphology of a new aggregation-inducedemission compound derived from tetraphenylethylene and carbazole. New. J. Chem; 36: 685–693.
  • [37]. Dong, YQ, Lam, JWY, Qin, AJ, Sun, JX, Liu, JZ, Li, Z, Sun, JZ, Sung, HHY, Williams, ID, Kwok, HS, Tang, BZ. 2007. Aggregation-induced andcrystallization-enhanced emissions of 1,2-diphenyl-3,4-bis(diphenylmethylene)-1-cyclobutene. Chem. Commun; 3255–3257.
  • [38]. Duraimurugan, K, Balasaravanan, R, Siva, A. 2016. Electron rich triphenylamine derivatives (D-π-D) for selective sensing of picric acid in aqueous media. Sensors and Actuators B; 231: 302–312.

Triphenylamine-Based Solid-State Emissive Fluorene Derivative with Aggregation-Induced Emission Enhancement Characteristics

Year 2024, Volume: 20 Issue: 3, 100 - 105, 30.09.2024
https://doi.org/10.18466/cbayarfbe.1516889

Abstract

Aggregation-induced emission (AIE) has garnered considerable attention in recent years. Understanding the mechanisms underlying AIE phenomena is crucial. Here, we present the design and synthesis of a novel fluorene derivative (4) based on triphenylamine, which exhibits typical AIE properties. The structure of it was totally characterized using FT-IR, MALDI-TOF mass analysis, elemental analysis, 1H, and 13C NMR spectroscopy. It displayed strong solid-state emission with diverse fluorescence characteristics. The AIE property of the compound was systematically studied using photoluminescence spectroscopy, revealing a distinct yellow light-emitting phenomenon. The solid-state luminescence showed a red shift of 148 nm compared to its luminescence in dilute dimethylformamide (DMF) solutions. Moreover, photophysical characteristics, including absorption and emission spectra, as well as fluorescence lifetime, were examined using UV–vis absorption and fluorescence emission spectroscopy. Compound (4) exhibited superior photosensitization abilities in both solid and solution states, with a notably enhanced effect observed in the solid state compared to the solution state.

Ethical Statement

There are no ethical issues after the publication of this manuscript.

References

  • [1]. Zhao, Z, Lam, JWY, Tang, BZ. 2012. Tetraphenylethene: a versatile AIE building block for the construction of efficient luminescent materials for organic light emitting diodes. J Mater Chem; 22:23726-40.
  • [2]. Huang, J, Yang, X, Li, X, Chen, P, Tang, R, Li, F, Lu, P, Ma, Y, Wang, L, Qin, J, Li, Q, Li, Z. 2012. Bipolar AIE-active luminogens comprised of an oxadiazole core and terminal TPE moieties as a new type of host for doped electroluminescence. Chem Commun; 48: 9586-8.
  • [3]. Martinez-Manez, R, Sancenon, F. 2003. Fluorogenic and chromogenic chemosensors and reagents for anions. Chem. Rev; 103(11): 4419-4476.
  • [4]. Wang, M, Zhang, G, Zhang, D, Zhu, D, Tang, BZ. 2010. Fluorescent bio/chemosensors based on silole and tetraphenylethene luminogens with aggregation-induced emission feature. J. Mater. Chem; 20: 1858.
  • [5]. Yang, Y, Zhao, Q, Feng, W, Li, F. 2013. Luminescent chemodosimeters for bioimaging. Chem. Rev; 113: 192.
  • [6]. Zhang, Q, Yu, P, Fan, Y, Sun, C, He, H, Liu, X, Lu, L, Zhao, M, Zhang, H, Zhang, F. 2020. Bright and stable NIR-II J-aggregated AIE dibodipy-based fluorescent probe for dynamic in vivo bioimaging. Angew. Chem., Int. Ed.; 60: 3967.
  • [7]. Shimizu, M, Takeda, Y, Higashi, M, Hiyama, T. 2009. 1,4-Bis(alkenyl)-2,5-dipiperidinobenzenes: minimal fluorophores exhibiting highly efficient emission in the solid state. Angew Chem Int Ed; 48: 3653-6.
  • [8] Xue, P, Sun, J, Chen, P, Gong, P, Yao, B, Zhang, Z, Qian, C, Lu, R. 2015. Strong solid emission and mechanofluorochromism of carbazole-based terephthalate derivatives adjusted by alkyl chains. J Mater Chem C; 3: 4086-92.
  • [9]. Yuan, WZ, Lu, P, Chen, S, Lam, JW, Wang, Z, Liu, Y, Kwok, HS, Ma, Y, Tang, BZ. 2010. Changing the behavior of chromophores from aggregation-caused quenching to aggregation-induced emission: development of highly efficient light emitters in the solid state. Adv Mater; 22: 2159-63.
  • [10]. Domaille, DW, Que, EL, Chang, CJ. 2008. Synthetic fluorescent sensors for studying the cell biology of metals. Nature Chemical Biology; 4: 168–175.
  • [11]. Hong, YN, Lam, JWY, Tang, BZ. 2011. Aggregation-induced emission. Chem. Soc. Rev; 40: 5361–5388.
  • [12]. Hong, YN, Lam, JWY, Tang, BZ. 2009. Aggregation-induced emission: phenomenon, mechanism and applications. Chem. Commun; 4332-4353.
  • [13]. Kwok, RTK, Leung, CWT, Lam, JWY, Tang, BZ. 2015. Chem. Soc. Rev; 44: 4228–4238.
  • [14]. Mei, J, Hong, Y, Lam, JWY, Qin, A, Tang, Y, Tang, BZ. 2014. Aggregation-Induced Emission: The Whole Is More Brilliant than the Parts. Adv. Mater; 26: 5429–5479.
  • [15]. Luo, J, Xie, Z, Lam, JWY, Cheng, L, Chen, H, Qiu, C, Kwok, HS, Zhan, X, Liu, Y, Zhu, D, Tang, BZ. 2001. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem. Commun; 1740–1741.
  • [16]. Kumbhar, HS, Shankarling, GS. 2015. Aggregation induced emission (AIE) active β-ketoiminate boron complexes: synthesis, photophysical and electrochemical properties. Dyes Pigments; 122: 85-93.
  • [17]. Kumar, M, Vij, V, Bhalla, V. 2012. Vapor-phase detection of trinitrotoluene by AIEE active hetero-oligophenylene-based carbazole derivatives. Langmuir; 28: 12417-21.
  • [18]. Shi, C, Guo, Z, Yan, Y, Zhu, S, Xie, Y, Zhao, YS, Zhu, W, Tian, H. 2013. Self-assembly solid-state enhanced red emission of quinolinemalononitrile: optical waveguides and stimuli response. ACS Appl. Mater. Interfaces; 5(1): 192-8.
  • [19]. Gu, X, Yao, J, Zhang, G, Zhang, C, Yan, Y, Zhao, Y, Zhang, D. 2013. New electron-donor/acceptor-substituted tetraphenylethylenes: aggregation-induced emission with tunable emission color and optical-waveguide behavior. Chem Asian J; 8(10): 2362-9.
  • [20]. Xu, F, Wang, H, Du, X, Wang, W, Wang, DE, Chen, S, Han, X, Li, N, Yuan, MS, Wang, J. 2016. Structure, property and mechanism study of fluorenone-based AIE dyes. Dyes and Pigments; 129: 121-128.
  • [21]. Du, X, Su, H, Zhao, L, Xing, X, Wang, B, Qiu, D, Wang, J, Yuan, MS. 2021. AIE-based donor–acceptor–donor fluorenone compound as multi-functional luminescence materials. Mater. Chem. Front; 5: 7508-7517.
  • [22]. Shaya, J, Corridon, PR, Al-Omari, B, Aoudi, A, Shunnar, A, Mohideen, MIH, Qurashi, A, Michel, BY, Burger, A. 2022. Design, photophysical properties, and applications of fluorene-based fluorophores in two-photon fluorescence bioimaging: A review. Journal of Photochemistry and Photobiology C: Photochemistry Reviews; 52, 100529.
  • [23]. Abbel, R, Schenning, APHJ, Meijer, EW. 2009. Fluorene-based materials and their supramolecular properties. J. Polym. Sci. Part A: Polym. Chem; 47: 4215–4233.
  • [24]. Moura, GLC, Simas, AM. 2010. Two-photon absorption by fluorene derivatives: systematic molecular design. J. Phys. Chem. C; 114(13): 6106–6116.
  • [25]. Kurdyukova, IV, Ishchenko AA. 2012. Organic dyes based on fluorene and its derivatives. Russ. Chem. Rev; 81: 258–290.
  • [26]. Ogawa, K. 2014. Two-photon absorbing molecules as potential materials for 3D optical memory. Appl. Sci; 4 (1): 1–18.
  • [27]. Lin, Y, Chen, Y, Ye, TL, Chen, ZK, Dai, YF, Ma, DG. 2012. Oligofluorene-based push–pull type functional materials for blue light-emitting diodes, J. Photochem. Photobiol. A: Chem; 230(1): 55-64.
  • [28]. Lim, K, Kim, C, Song, J, Yu, T, Lim, W, Song, K, Wang, P, Zu, N, Ko, J. 2011. Enhancing the performance of organic dye-sensitized solar cells via a slight structure modification. J. Phys. Chem. C; 115: 22640–22646.
  • [29]. Erdoğan, M, Horoz, S. 2021. Synthesis and characterization of a triphenylamine-dibenzosuberenone-based conjugated organic material and an investigation of its photovoltaic properties. Journal of Chemical Research; 45(1-2): 207-212.
  • [30]. Erdoğan, M, Orhan, Z, Daş, E. 2022. Synthesis of electron-rich thiophene triphenylamine based organic material for photodiode applications. Optical Materials; 128:12446.
  • [31]. Chen, ZQ, Chen, T, Liu, JX, Zhang, GF, Li, C, Gong, WL, Xiong ZJ, Xie, NH, Tang, BZ, Zhu, MQ. 2015. Geminal cross-coupling of 1, 1-dibromoolefins facilitating multiple topological π-conjugated tetraarylethenes. Macromolecules; 48(21): 7823-7835.
  • [32]. Yildirim-Sarikaya, S, Ardic-Alidagi, H, Cetindere, S. 2023. Novel BODIPY‑Fluorene‑Fullerene and BODIPY‑Fluorene‑BODIPY Conjugates: Synthesis, Characterization, Photophysical and Photochemical Properties. Journal of Fluorescence; 33: 297–304.
  • [33]. Tan, S, Yin, Y, Chen, W, Chen, Z, Tian, W, Pu, S. 2020. Carbazole-based highly solid-state emissive fluorene derivatives with various mechanochromic fluorescence characteristics. Dyes and Pigments; 177: 108302.
  • [34]. Chen, Z, Liang, J, Han, X, Yin, J, Yu, GA, Liu, SH. 2015. Fluorene-based novel highly emissive fluorescent molecules with aggregate fluorescence change or aggregation-induced emission enhancement characteristics. Dyes and Pigments; 112: 59-66.
  • [35]. Gouthaman, S, Jayaraj, A, Sugunalakshmi, M, Sivaraman, G, Swamy, PCA. 2022. Supramolecular self-assembly mediated aggregation-induced emission of fluorene-derived cyanostilbenes: multifunctional probes for live cell-imaging. J. Mater. Chem. B; 10: 2238.
  • [36]. Zhou, X, Li, H, Chi, Z, Zhang, X, Zhang, J, Xu, B, Zhang, Y, Liu, S, Xu, J. 2012. Piezofluorochromism and morphology of a new aggregation-inducedemission compound derived from tetraphenylethylene and carbazole. New. J. Chem; 36: 685–693.
  • [37]. Dong, YQ, Lam, JWY, Qin, AJ, Sun, JX, Liu, JZ, Li, Z, Sun, JZ, Sung, HHY, Williams, ID, Kwok, HS, Tang, BZ. 2007. Aggregation-induced andcrystallization-enhanced emissions of 1,2-diphenyl-3,4-bis(diphenylmethylene)-1-cyclobutene. Chem. Commun; 3255–3257.
  • [38]. Duraimurugan, K, Balasaravanan, R, Siva, A. 2016. Electron rich triphenylamine derivatives (D-π-D) for selective sensing of picric acid in aqueous media. Sensors and Actuators B; 231: 302–312.
There are 38 citations in total.

Details

Primary Language English
Subjects Inorganic Materials
Journal Section Articles
Authors

Seda Çetindere 0000-0001-7599-8491

Musa Erdoğan 0000-0001-6097-2862

Publication Date September 30, 2024
Submission Date July 16, 2024
Acceptance Date September 26, 2024
Published in Issue Year 2024 Volume: 20 Issue: 3

Cite

APA Çetindere, S., & Erdoğan, M. (2024). Triphenylamine-Based Solid-State Emissive Fluorene Derivative with Aggregation-Induced Emission Enhancement Characteristics. Celal Bayar University Journal of Science, 20(3), 100-105. https://doi.org/10.18466/cbayarfbe.1516889
AMA Çetindere S, Erdoğan M. Triphenylamine-Based Solid-State Emissive Fluorene Derivative with Aggregation-Induced Emission Enhancement Characteristics. CBUJOS. September 2024;20(3):100-105. doi:10.18466/cbayarfbe.1516889
Chicago Çetindere, Seda, and Musa Erdoğan. “Triphenylamine-Based Solid-State Emissive Fluorene Derivative With Aggregation-Induced Emission Enhancement Characteristics”. Celal Bayar University Journal of Science 20, no. 3 (September 2024): 100-105. https://doi.org/10.18466/cbayarfbe.1516889.
EndNote Çetindere S, Erdoğan M (September 1, 2024) Triphenylamine-Based Solid-State Emissive Fluorene Derivative with Aggregation-Induced Emission Enhancement Characteristics. Celal Bayar University Journal of Science 20 3 100–105.
IEEE S. Çetindere and M. Erdoğan, “Triphenylamine-Based Solid-State Emissive Fluorene Derivative with Aggregation-Induced Emission Enhancement Characteristics”, CBUJOS, vol. 20, no. 3, pp. 100–105, 2024, doi: 10.18466/cbayarfbe.1516889.
ISNAD Çetindere, Seda - Erdoğan, Musa. “Triphenylamine-Based Solid-State Emissive Fluorene Derivative With Aggregation-Induced Emission Enhancement Characteristics”. Celal Bayar University Journal of Science 20/3 (September 2024), 100-105. https://doi.org/10.18466/cbayarfbe.1516889.
JAMA Çetindere S, Erdoğan M. Triphenylamine-Based Solid-State Emissive Fluorene Derivative with Aggregation-Induced Emission Enhancement Characteristics. CBUJOS. 2024;20:100–105.
MLA Çetindere, Seda and Musa Erdoğan. “Triphenylamine-Based Solid-State Emissive Fluorene Derivative With Aggregation-Induced Emission Enhancement Characteristics”. Celal Bayar University Journal of Science, vol. 20, no. 3, 2024, pp. 100-5, doi:10.18466/cbayarfbe.1516889.
Vancouver Çetindere S, Erdoğan M. Triphenylamine-Based Solid-State Emissive Fluorene Derivative with Aggregation-Induced Emission Enhancement Characteristics. CBUJOS. 2024;20(3):100-5.