Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 71, Pages 16294-16300Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201903100
Keywords
carbazoles; photochemistry; room-temperature phosphorescence; solid-state emission; spin-orbit coupling
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Funding
- Center of Innovation (COI) Program from the Japan Science and Technology Agency, JST
- JSPS [17H03131]
- Grants-in-Aid for Scientific Research [17H03131] Funding Source: KAKEN
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Exploration of pure metal-free organic molecules that exhibit strong room-temperature phosphorescence (RTP) is an emerging research topic. In this regard, unveiling the design principles for an efficient RTP molecule is an essential, but challenging, task. A small molecule is an ideal platform to precisely understand the fundamental role of each functional component because the parent molecule can be easily derivatized. Here, the RTP behaviors of a series of 3-pyridylcarbazole derivatives are presented. Experimental studies in combination with theoretical calculations reveal the crucial role of the n orbital on the central pyridine ring in the dramatic enhancement of the intersystem crossing between the charge-transfer-excited singlet state and the locally excited triplet states. Single-crystal X-ray crystallographic studies apparently indicate that both the pyridine ring and fluorine atom contribute to the enhancement of the RTP because of the restricted motion owing to weak C-H...N and H...F hydrogen-bonding interactions. The single crystal of the fluorine-substituted derivative shows an ultra-long phosphorescent lifetime (tau(P)) of 1.1 s and a phosphorescence quantum yield (phi(P)) of 1.2 %, whereas the bromine-substituted derivative exhibits tau(P) of 0.15 s with a phi(P) of 7.9 %. We believe that this work provides a fundamental and universal guideline for the generation of pure organic molecules exhibiting strong RTP.
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