Excited‐State Symmetry Breaking in an Aza‐Nanographene Dye
The photophysics of a structurally unique aza‐analogue of polycyclic aromatic hydrocarbons characterized by 12 conjugated rings and a curved architecture was studied in detail. The combined experimental and computational investigation reveals that the lowest excited state has charge‐transfer charact...
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| Published in | Chemistry : a European journal Vol. 25; no. 61; pp. 13930 - 13938 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Germany
Wiley Subscription Services, Inc
04.11.2019
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| Abstract | The photophysics of a structurally unique aza‐analogue of polycyclic aromatic hydrocarbons characterized by 12 conjugated rings and a curved architecture was studied in detail. The combined experimental and computational investigation reveals that the lowest excited state has charge‐transfer character, in spite of the absence of any peripheral electron‐withdrawing groups. The exceptionally electron‐rich core comprised of two fused pyrrole rings is responsible for it. The observed strong solvatofluorochromism is related to symmetry breaking occurring in the emitting excited state, leading to a significant dipole moment (13.5 D) in the relaxed excited state. The anomalously small fluorescence anisotropy of this molecule, which is qualitatively different from what is observed in standard quadrupolar dyes, is explained as due to the presence of excited states that are close in energy but have different polarization directions.
The emission solvatochromism of a centrosymmetric double helical π‐expanded pyrrolo[3,2‐b]pyrrole is related to symmetry breaking of the first excited state. Strong emission from the charge‐transfer state is interpreted as borrowing intensity from the close‐lying localized transitions, thus explaining the high and stable fluorescence quantum yield. |
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| AbstractList | The photophysics of a structurally unique aza‐analogue of polycyclic aromatic hydrocarbons characterized by 12 conjugated rings and a curved architecture was studied in detail. The combined experimental and computational investigation reveals that the lowest excited state has charge‐transfer character, in spite of the absence of any peripheral electron‐withdrawing groups. The exceptionally electron‐rich core comprised of two fused pyrrole rings is responsible for it. The observed strong solvatofluorochromism is related to symmetry breaking occurring in the emitting excited state, leading to a significant dipole moment (13.5 D) in the relaxed excited state. The anomalously small fluorescence anisotropy of this molecule, which is qualitatively different from what is observed in standard quadrupolar dyes, is explained as due to the presence of excited states that are close in energy but have different polarization directions. Abstract The photophysics of a structurally unique aza‐analogue of polycyclic aromatic hydrocarbons characterized by 12 conjugated rings and a curved architecture was studied in detail. The combined experimental and computational investigation reveals that the lowest excited state has charge‐transfer character, in spite of the absence of any peripheral electron‐withdrawing groups. The exceptionally electron‐rich core comprised of two fused pyrrole rings is responsible for it. The observed strong solvatofluorochromism is related to symmetry breaking occurring in the emitting excited state, leading to a significant dipole moment (13.5 D) in the relaxed excited state. The anomalously small fluorescence anisotropy of this molecule, which is qualitatively different from what is observed in standard quadrupolar dyes, is explained as due to the presence of excited states that are close in energy but have different polarization directions. The photophysics of a structurally unique aza‐analogue of polycyclic aromatic hydrocarbons characterized by 12 conjugated rings and a curved architecture was studied in detail. The combined experimental and computational investigation reveals that the lowest excited state has charge‐transfer character, in spite of the absence of any peripheral electron‐withdrawing groups. The exceptionally electron‐rich core comprised of two fused pyrrole rings is responsible for it. The observed strong solvatofluorochromism is related to symmetry breaking occurring in the emitting excited state, leading to a significant dipole moment (13.5 D) in the relaxed excited state. The anomalously small fluorescence anisotropy of this molecule, which is qualitatively different from what is observed in standard quadrupolar dyes, is explained as due to the presence of excited states that are close in energy but have different polarization directions. The emission solvatochromism of a centrosymmetric double helical π‐expanded pyrrolo[3,2‐b]pyrrole is related to symmetry breaking of the first excited state. Strong emission from the charge‐transfer state is interpreted as borrowing intensity from the close‐lying localized transitions, thus explaining the high and stable fluorescence quantum yield. |
| Author | Bardi, Brunella Gryko, Daniel T. Painelli, Anna Krzeszewski, Maciej Terenziani, Francesca |
| Author_xml | – sequence: 1 givenname: Brunella surname: Bardi fullname: Bardi, Brunella organization: University of Parma – sequence: 2 givenname: Maciej orcidid: 0000-0002-0940-7443 surname: Krzeszewski fullname: Krzeszewski, Maciej organization: Polish Academy of Sciences – sequence: 3 givenname: Daniel T. orcidid: 0000-0002-2146-1282 surname: Gryko fullname: Gryko, Daniel T. email: dtgryko@icho.edu.pl organization: Polish Academy of Sciences – sequence: 4 givenname: Anna orcidid: 0000-0002-3500-3848 surname: Painelli fullname: Painelli, Anna organization: University of Parma – sequence: 5 givenname: Francesca orcidid: 0000-0001-5162-9210 surname: Terenziani fullname: Terenziani, Francesca email: francesca.terenziani@unipr.it organization: University of Parma |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31373409$$D View this record in MEDLINE/PubMed |
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| Keywords | polarized spectroscopy fused-ring systems computational chemistry solvatochromism charge transfer |
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| Snippet | The photophysics of a structurally unique aza‐analogue of polycyclic aromatic hydrocarbons characterized by 12 conjugated rings and a curved architecture was... The photophysics of a structurally unique aza-analogue of polycyclic aromatic hydrocarbons characterized by 12 conjugated rings and a curved architecture was... Abstract The photophysics of a structurally unique aza‐analogue of polycyclic aromatic hydrocarbons characterized by 12 conjugated rings and a curved... |
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| SubjectTerms | Anisotropy Broken symmetry Charge transfer Chemistry computational chemistry Computer applications Dipole moments Dyes Excitation Fluorescence fused-ring systems polarized spectroscopy Polycyclic aromatic hydrocarbons solvatochromism |
| Title | Excited‐State Symmetry Breaking in an Aza‐Nanographene Dye |
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