Theoretical investigations of the auxochromic effect on novel thermally activated delayed fluorescence (TADF) anthracene derivatives
Abstract Thermally active delayed fluorescence (TADF) of experimentally synthesized anthracene derivatives is studied. The studied compounds are named as 9-cyano-10-diphenylamino-anthracene (Cy-Anth-1), 9-(N-carbazolyl)-10-cyanoanthracene (Cy-Anth-2), 10-(benzofuro[2,3-b] pyridin-6-yl)-N, N-diphenyl...
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2025-02-01
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| Series: | BMC Chemistry |
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| Online Access: | https://doi.org/10.1186/s13065-025-01413-5 |
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| author | Sharif Abu Alrub Yaqoob Shah Muhammad Umar Asim Mansha Ahmed I. Ali Rageh K. Hussein |
| author_facet | Sharif Abu Alrub Yaqoob Shah Muhammad Umar Asim Mansha Ahmed I. Ali Rageh K. Hussein |
| author_sort | Sharif Abu Alrub |
| collection | DOAJ |
| description | Abstract Thermally active delayed fluorescence (TADF) of experimentally synthesized anthracene derivatives is studied. The studied compounds are named as 9-cyano-10-diphenylamino-anthracene (Cy-Anth-1), 9-(N-carbazolyl)-10-cyanoanthracene (Cy-Anth-2), 10-(benzofuro[2,3-b] pyridin-6-yl)-N, N-diphenylanthracen-9-amine (Benzo4-Anth-1), 6-(10-(9H-carbazol-9-yl) anthracen-9-yl) benzofuro[2,3-b] pyridine (Benzo4-Anth-2). Chemical characterization and the structure-TADF relationship were determined using the DFT and TD-DFT techniques. The analysis of frontier molecular orbitals and molecular electrostatic potential indicated that the Benzo4-Anth-1 derivative is a good candidate for TADF due to its spatially separated donor and acceptor groups. The energy gap ΔE (S1-T2) of Cy-Anth-1, Cy-Anth-2, Benzo4-Anth-1, and Benzo4-Anth-2 is 0.0057, -0.026, 0.0528, and -0.0635 eV, respectively. While ΔE (T2-T1) for Cy-Anth-1, Cy-Anth-2, Benzo4-Anth-1, and Benzo4-Anth-2 is 0.759, 0.790, 1.019, and 0.926 eV, respectively. Donor (D = (N, N-diphenyl)) and acceptor (A = (10-(benzofuro[2,3-b] pyridin-6-yl)) in D-π-A system enhances the ΔE (S1-S0) up to 2.837 eV and decreases ΔE (S1-T2) to -0.0635 eV by making it good TADF material. Thermodynamic investigation revealed that the rise in temperature from 50–500 K, CV, CP, internal energy (U), enthalpy (H), entropy (S), and ln (Q) increases, but Gibbs free energy (G) decreases. |
| format | Article |
| id | doaj-art-48c8331b29ae4973b2619c21c8a0a1f3 |
| institution | OA Journals |
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| language | English |
| publishDate | 2025-02-01 |
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| spelling | doaj-art-48c8331b29ae4973b2619c21c8a0a1f32025-08-20T02:15:06ZengBMCBMC Chemistry2661-801X2025-02-0119111410.1186/s13065-025-01413-5Theoretical investigations of the auxochromic effect on novel thermally activated delayed fluorescence (TADF) anthracene derivativesSharif Abu Alrub0Yaqoob Shah1Muhammad Umar2Asim Mansha3Ahmed I. Ali4Rageh K. Hussein5Department of Physics, College of Science, Imam Mohammad Ibn Saud Islamic University (IMSIU)Department of Chemistry, National Textile UniversityDepartment of Chemistry, Government College University FaisalabadDepartment of Chemistry, Government College University FaisalabadBasic Science Department, Faculty of Technology and Education, Helwan UniversityDepartment of Physics, College of Science, Imam Mohammad Ibn Saud Islamic University (IMSIU)Abstract Thermally active delayed fluorescence (TADF) of experimentally synthesized anthracene derivatives is studied. The studied compounds are named as 9-cyano-10-diphenylamino-anthracene (Cy-Anth-1), 9-(N-carbazolyl)-10-cyanoanthracene (Cy-Anth-2), 10-(benzofuro[2,3-b] pyridin-6-yl)-N, N-diphenylanthracen-9-amine (Benzo4-Anth-1), 6-(10-(9H-carbazol-9-yl) anthracen-9-yl) benzofuro[2,3-b] pyridine (Benzo4-Anth-2). Chemical characterization and the structure-TADF relationship were determined using the DFT and TD-DFT techniques. The analysis of frontier molecular orbitals and molecular electrostatic potential indicated that the Benzo4-Anth-1 derivative is a good candidate for TADF due to its spatially separated donor and acceptor groups. The energy gap ΔE (S1-T2) of Cy-Anth-1, Cy-Anth-2, Benzo4-Anth-1, and Benzo4-Anth-2 is 0.0057, -0.026, 0.0528, and -0.0635 eV, respectively. While ΔE (T2-T1) for Cy-Anth-1, Cy-Anth-2, Benzo4-Anth-1, and Benzo4-Anth-2 is 0.759, 0.790, 1.019, and 0.926 eV, respectively. Donor (D = (N, N-diphenyl)) and acceptor (A = (10-(benzofuro[2,3-b] pyridin-6-yl)) in D-π-A system enhances the ΔE (S1-S0) up to 2.837 eV and decreases ΔE (S1-T2) to -0.0635 eV by making it good TADF material. Thermodynamic investigation revealed that the rise in temperature from 50–500 K, CV, CP, internal energy (U), enthalpy (H), entropy (S), and ln (Q) increases, but Gibbs free energy (G) decreases.https://doi.org/10.1186/s13065-025-01413-5Thermally active delayed fluorescenceInternal quantum efficiencyReverse intersystem crossingDFT & TD-DFT |
| spellingShingle | Sharif Abu Alrub Yaqoob Shah Muhammad Umar Asim Mansha Ahmed I. Ali Rageh K. Hussein Theoretical investigations of the auxochromic effect on novel thermally activated delayed fluorescence (TADF) anthracene derivatives BMC Chemistry Thermally active delayed fluorescence Internal quantum efficiency Reverse intersystem crossing DFT & TD-DFT |
| title | Theoretical investigations of the auxochromic effect on novel thermally activated delayed fluorescence (TADF) anthracene derivatives |
| title_full | Theoretical investigations of the auxochromic effect on novel thermally activated delayed fluorescence (TADF) anthracene derivatives |
| title_fullStr | Theoretical investigations of the auxochromic effect on novel thermally activated delayed fluorescence (TADF) anthracene derivatives |
| title_full_unstemmed | Theoretical investigations of the auxochromic effect on novel thermally activated delayed fluorescence (TADF) anthracene derivatives |
| title_short | Theoretical investigations of the auxochromic effect on novel thermally activated delayed fluorescence (TADF) anthracene derivatives |
| title_sort | theoretical investigations of the auxochromic effect on novel thermally activated delayed fluorescence tadf anthracene derivatives |
| topic | Thermally active delayed fluorescence Internal quantum efficiency Reverse intersystem crossing DFT & TD-DFT |
| url | https://doi.org/10.1186/s13065-025-01413-5 |
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