Excimer Disaggregation Enhanced Emission: A Fluorescence "Turn-On" Approach to Oxoanion Recognition

Journal of the American Chemical Society
Jian YangHan-Yuan Gong

Abstract

A new approach to anion sensing that involves excimer disaggregation induced emission (EDIE) is reported. It involves the anion-mediated disaggregation of the excimer formed from a cationic macrocycle. This leads to an increase in the observed fluorescence intensity. The macrocycle in question, cyclo[1] N2, N6-dimethyl- N2, N6-bis(6-(1 H-imidazolium-1-yl)pyridin-2-yl)pyridine-2,6-diamine[1]1,4-dimethylbenzene (12+; prepared as its PF6- salt), is obtained in ca. 70% yield via a simple cyclization. X-ray diffraction analyses of single crystals revealed that, as prepared, this macrocycle exists in a supramolecular polymeric form in the solid state. Macrocycle 12+ is weakly fluorescent in acetonitrile. The emission intensity is concentration dependent, with the maximum intensity being observed at [12+] ≈ 0.020 mM. This finding is ascribed to formation of an excimer, followed possibly by higher order aggregates as the concentration of 12+ is increased. Addition of tetrabutylammonium pyrophosphate (HP2O73-) to 12+ (0.020 mM in acetonitrile) produces a ca. 200-fold enhancement in the emission intensity (λex = 334 nm; λem = 390-650 nm). These findings are rationalized in terms of the HP2O73- serving to break up essentially non-fluoresc...Continue Reading

References

Dec 19, 2001·Accounts of Chemical Research·S L WiskurE V Anslyn
Nov 13, 2003·Chemical Reviews·Ramón Martínez-Máñez, Félix Sancenón
Dec 11, 2003·Organic & Biomolecular Chemistry·Jonathan L SesslerVincent Lynch
Jan 17, 2004·The Journal of Organic Chemistry·Juyoung YoonKwang S Kim
Aug 11, 2005·Journal of the American Chemical Society·Jonathan L SesslerYuri A Ustynyuk
Apr 6, 2006·Journal of the American Chemical Society·Iwao SuzukiAkiyo Yamauchi
Dec 13, 2006·Angewandte Chemie·Anna K H HirschFrançois Diederich
Dec 30, 2006·The Journal of Organic Chemistry·Yunkou WuShiguo Sun
Nov 16, 2007·Organic Letters·Carsten Reyheller, Stefan Kubik
Sep 19, 2008·Accounts of Chemical Research·Sook Kyung KimJuyoung Yoon
Mar 5, 2009·Chemical Communications : Chem Comm·Cong Yu, Vivian Wing-Wah Yam
Aug 26, 2010·Chemical Society Reviews·Ai-Fang LiYun-Bao Jiang
Sep 8, 2010·Chemical Society Reviews·Carla BazzicalupiVito Lippolis
Nov 11, 2010·Organic & Biomolecular Chemistry·Nicholas H Evans, Paul D Beer
Feb 1, 2011·Chemical Society Reviews·María E MoraguesFélix Sancenón
Jul 12, 2011·Chemical Communications : Chem Comm·Nicholas H EvansPaul D Beer
Jul 22, 2011·Organic Letters·Qian-Yong CaoJong Seung Kim
Sep 14, 2011·Chemical Reviews·Amanda E HargroveEric V Anslyn
Dec 14, 2011·Luminescence : the Journal of Biological and Chemical Luminescence·Jiang-Shan ShenYun-Bao Jiang
Jul 6, 2012·Chemical Communications : Chem Comm·Ji Young JungJuyoung Yoon
Feb 13, 2013·Chemical Society Reviews·Luis E Santos-FigueroaFélix Sancenón
Dec 5, 2013·Chemical Communications : Chem Comm·Hai-Xia LiuLiang Zhao
Feb 12, 2014·Chemical Society Reviews·Duanting ZhaiYoung-Tae Chang
Apr 16, 2014·Chemical Society Reviews·Rongrong HuBen Zhong Tang
May 30, 2014·Chemical Society Reviews·Jiajia Cai, Jonathan L Sessler
Jul 1, 2014·Chemical Society Reviews·Philip A Gale, Claudia Caltagirone
Jan 13, 2015·Chemical Society Reviews·Songyi LeeJuyoung Yoon
Feb 24, 2015·Angewandte Chemie·Chunhua RenZhimou Yang

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Citations

May 14, 2021·Organic & Biomolecular Chemistry·Hui Min Tay, Paul Beer
Jun 11, 2021·Coordination Chemistry Reviews·Chenxing GuoJonathan L Sessler
Nov 20, 2019·The Journal of Organic Chemistry·Jinrok Oh, Jong-In Hong
Nov 3, 2021·Chemical Communications : Chem Comm·Qiang ShiLeyong Wang

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