Dibenzoquinone Cyclopentadithiophene Diradicaloids Show Optical Transitions of Different Spin States and Anomalous Near‐Infrared Emission
We have prepared a series of bis(semiquinone) compounds with dithiophene bridges of different length that evolve from closed‐shell (smaller compound) to full diradical (longer compound) for which the narrow singlet‐triplet energy gap allows the triplet population at 298 K. The medium size system has...
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| Published in: | Angewandte Chemie |
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29-10-2024
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| Abstract | We have prepared a series of bis(semiquinone) compounds with dithiophene bridges of different length that evolve from closed‐shell (smaller compound) to full diradical (longer compound) for which the narrow singlet‐triplet energy gap allows the triplet population at 298 K. The medium size system has a variety of photonic properties with absorptions and emission in the optical near‐infrared region mediated by a unique case of anti‐Kasha emission. A whole set of optical absorption/emission and vibrational steady state spectroscopies as well as picosecond transient absorption spectroscopy, all complemented with spectroelectrochemistry and theoretical calculations, is presented. |
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| AbstractList | We have prepared a series of bis(semiquinone) compounds with dithiophene bridges of different length that evolve from closed‐shell (smaller compound) to full diradical (longer compound) for which the narrow singlet‐triplet energy gap allows the triplet population at 298 K. The medium size system has a variety of photonic properties with absorptions and emission in the optical near‐infrared region mediated by a unique case of anti‐Kasha emission. A whole set of optical absorption/emission and vibrational steady state spectroscopies as well as picosecond transient absorption spectroscopy, all complemented with spectroelectrochemistry and theoretical calculations, is presented. |
| Author | de La Cruz, Pilar Barrejón, Myriam Casado, Juan P. M., Janaarthana Babu Privado, María Casanova, David Moles Quintero, Sergio Langa, Fernando |
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| Cites_doi | 10.2307/3571331 10.1021/cr8004229 10.1021/jacs.0c09588 10.1039/C4SC01769B 10.1002/adma.201001170 10.1039/C8CP04008G 10.1007/978-3-319-08120-5 10.1021/acs.accounts.3c00214 10.1002/9780470745533 10.1002/0470845767 10.1021/acs.accounts.7b00004 10.1021/acs.jpclett.5b00198 10.1021/jacs.8b01884 10.1002/adma.200305200 10.1021/jp055455v 10.1021/ja5125463 10.1021/jacs.0c06604 10.1351/pac199769040785 10.1021/ja025553j 10.1021/jacs.5b05940 10.1021/jacs.3c05251 10.1021/jacs.3c05009 10.1002/chem.202300388 10.1021/ja2073643 10.1021/ja027161i 10.1021/jacs.3c13270 10.1021/jp960852e 10.1021/ja2061903 10.1039/C5SC04706D 10.1002/anie.201605893 10.1021/ja101015q 10.1002/anie.200703244 10.1021/jacs.5b03899 10.1021/ja061372w 10.1021/acs.jpclett.5b02792 10.1039/C7SC02756G 10.1021/ja309599m 10.1021/acs.chemrev.5b00165 10.1039/c2cs35079c 10.1021/ja1049737 10.1021/ja051840m 10.1021/ja3072385 10.1002/anie.201904153 10.1021/ja3003183 10.1002/anie.198701701 10.1002/adma.200903152 10.1063/1.1742314 10.1016/0009-2614(75)80169-2 10.1021/jp0138678 10.1038/s41563-020-0705-9 |
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| References | e_1_2_3_50_1 e_1_2_3_16_2 e_1_2_3_37_2 e_1_2_3_4_1 e_1_2_3_18_1 e_1_2_3_2_2 e_1_2_3_39_2 e_1_2_3_12_1 e_1_2_3_56_2 e_1_2_3_58_1 e_1_2_3_33_2 e_1_2_3_6_2 e_1_2_3_14_2 e_1_2_3_52_2 e_1_2_3_10_2 e_1_2_3_31_2 e_1_2_3_54_1 e_1_2_3_60_2 e_1_2_3_62_1 e_1_2_3_49_1 e_1_2_3_28_2 e_1_2_3_22_2 e_1_2_3_24_1 e_1_2_3_45_1 e_1_2_3_47_2 e_1_2_3_26_1 e_1_2_3_68_1 e_1_2_3_64_2 e_1_2_3_41_1 e_1_2_3_66_1 e_1_2_3_20_2 e_1_2_3_43_2 e_1_2_3_51_1 Xhang C. (e_1_2_3_8_2) 2020; 30 e_1_2_3_1_1 e_1_2_3_19_2 e_1_2_3_5_2 e_1_2_3_15_2 e_1_2_3_38_2 e_1_2_3_3_2 e_1_2_3_17_2 e_1_2_3_9_2 e_1_2_3_11_2 e_1_2_3_34_2 e_1_2_3_57_1 e_1_2_3_55_2 e_1_2_3_59_1 e_1_2_3_13_2 e_1_2_3_7_1 e_1_2_3_36_1 e_1_2_3_30_2 e_1_2_3_32_1 e_1_2_3_53_2 Wegner G. (e_1_2_3_35_1) 1996 e_1_2_3_61_2 e_1_2_3_40_1 e_1_2_3_27_2 e_1_2_3_29_2 e_1_2_3_23_1 e_1_2_3_44_2 e_1_2_3_25_1 e_1_2_3_48_1 e_1_2_3_67_1 e_1_2_3_46_2 e_1_2_3_42_1 e_1_2_3_65_1 e_1_2_3_21_2 e_1_2_3_63_2 |
| References_xml | – ident: e_1_2_3_4_1 – ident: e_1_2_3_18_1 – ident: e_1_2_3_44_2 doi: 10.2307/3571331 – ident: e_1_2_3_5_2 doi: 10.1021/cr8004229 – ident: e_1_2_3_65_1 doi: 10.1021/jacs.0c09588 – ident: e_1_2_3_31_2 doi: 10.1039/C4SC01769B – ident: e_1_2_3_51_1 – ident: e_1_2_3_15_2 doi: 10.1002/adma.201001170 – ident: e_1_2_3_50_1 doi: 10.1039/C8CP04008G – ident: e_1_2_3_12_1 – ident: e_1_2_3_53_2 doi: 10.1007/978-3-319-08120-5 – ident: e_1_2_3_9_2 doi: 10.1021/acs.accounts.3c00214 – ident: e_1_2_3_2_2 doi: 10.1002/9780470745533 – ident: e_1_2_3_57_1 doi: 10.1002/0470845767 – ident: e_1_2_3_10_2 doi: 10.1021/acs.accounts.7b00004 – ident: e_1_2_3_26_1 – ident: e_1_2_3_19_2 doi: 10.1021/acs.jpclett.5b00198 – ident: e_1_2_3_21_2 doi: 10.1021/jacs.8b01884 – ident: e_1_2_3_42_1 – ident: e_1_2_3_14_2 doi: 10.1002/adma.200305200 – ident: e_1_2_3_34_2 doi: 10.1021/jp055455v – ident: e_1_2_3_64_2 doi: 10.1021/ja5125463 – ident: e_1_2_3_59_1 – ident: e_1_2_3_20_2 doi: 10.1021/jacs.0c06604 – ident: e_1_2_3_41_1 doi: 10.1351/pac199769040785 – ident: e_1_2_3_13_2 doi: 10.1021/ja025553j – volume: 30 year: 2020 ident: e_1_2_3_8_2 publication-title: Adv. Funct. Mater. contributor: fullname: Xhang C. – ident: e_1_2_3_22_2 doi: 10.1021/jacs.5b05940 – ident: e_1_2_3_46_2 doi: 10.1021/jacs.3c05251 – ident: e_1_2_3_48_1 doi: 10.1021/jacs.3c05009 – ident: e_1_2_3_67_1 doi: 10.1002/chem.202300388 – ident: e_1_2_3_3_2 doi: 10.1021/ja2073643 – ident: e_1_2_3_63_2 doi: 10.1021/ja027161i – ident: e_1_2_3_32_1 – ident: e_1_2_3_47_2 doi: 10.1021/jacs.3c13270 – ident: e_1_2_3_33_2 doi: 10.1021/jp960852e – ident: e_1_2_3_28_2 doi: 10.1021/ja2061903 – ident: e_1_2_3_1_1 – ident: e_1_2_3_7_1 – ident: e_1_2_3_58_1 doi: 10.1021/ja2061903 – ident: e_1_2_3_30_2 doi: 10.1039/C5SC04706D – ident: e_1_2_3_60_2 doi: 10.1002/anie.201605893 – ident: e_1_2_3_39_2 doi: 10.1021/ja101015q – ident: e_1_2_3_62_1 – volume-title: Electronic Materials: The Oligomer Approach year: 1996 ident: e_1_2_3_35_1 contributor: fullname: Wegner G. – ident: e_1_2_3_54_1 – ident: e_1_2_3_29_2 doi: 10.1002/anie.200703244 – ident: e_1_2_3_38_2 doi: 10.1021/jacs.5b03899 – ident: e_1_2_3_37_2 doi: 10.1021/ja061372w – ident: e_1_2_3_68_1 doi: 10.1021/acs.jpclett.5b02792 – ident: e_1_2_3_45_1 – ident: e_1_2_3_25_1 doi: 10.1039/C7SC02756G – ident: e_1_2_3_55_2 doi: 10.1021/ja309599m – ident: e_1_2_3_36_1 – ident: e_1_2_3_6_2 doi: 10.1021/acs.chemrev.5b00165 – ident: e_1_2_3_11_2 doi: 10.1039/c2cs35079c – ident: e_1_2_3_56_2 doi: 10.1021/ja1049737 – ident: e_1_2_3_27_2 doi: 10.1002/anie.201605893 – ident: e_1_2_3_23_1 doi: 10.1021/ja051840m – ident: e_1_2_3_24_1 doi: 10.1021/ja3072385 – ident: e_1_2_3_61_2 doi: 10.1002/anie.201904153 – ident: e_1_2_3_17_2 doi: 10.1021/ja3003183 – ident: e_1_2_3_52_2 doi: 10.1002/anie.198701701 – ident: e_1_2_3_16_2 doi: 10.1002/adma.200903152 – ident: e_1_2_3_43_2 doi: 10.1063/1.1742314 – ident: e_1_2_3_49_1 doi: 10.1016/0009-2614(75)80169-2 – ident: e_1_2_3_66_1 doi: 10.1021/jp0138678 – ident: e_1_2_3_40_1 doi: 10.1038/s41563-020-0705-9 |
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| Title | Dibenzoquinone Cyclopentadithiophene Diradicaloids Show Optical Transitions of Different Spin States and Anomalous Near‐Infrared Emission |
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