Zero-Overlap Fluorophores for Fluorescent Studies at Any Concentration.

Journal of the American Chemical Society
Ayan DharaAmar H Flood

Abstract

Fluorophores are powerful tools for the study of chemistry, biology, and physics. However, fluorescence is severely impaired when concentrations climb above 5 μM as a result of effects like self-absorption and chromatic shifts in the emitted light. Herein, we report the creation of a charge-transfer (CT) fluorophore and the discovery that its emission color seen at low concentrations is unchanged even at 5 mM, some 3 orders of magnitude beyond typical limits. The fluorophore is composed of a triphenylamine-substituted cyanostar macrocycle, and it exhibits a remarkable Stokes shift of 15 000 cm-1 to generate emission at 633 nm. Crucial to the performance of this fluorophore is the observation that its emission spectrum shows near-zero overlap with the absorption band at 325 nm. We propose that reducing the spectral overlap to zero is a key to achieving full fluorescence across all concentrations. The triphenylamine donor and five cyanostilbene acceptor units of the macrocycle generate an emissive CT state. Unlike closely related donor-acceptor control compounds showing dual emission, the cyanostar framework inhibited emission from the second state to create a zero-overlap fluorophore. We demonstrated the use of emission spectros...Continue Reading

References

Feb 21, 1991·Nature·S R AdamsR Y Tsien
Sep 30, 2005·Journal of the American Chemical Society·Julia L BricksKnut Rurack
Oct 3, 2006·Angewandte Chemie·Ulrich RöschFrank Würthner
Dec 15, 2006·Journal of the American Chemical Society·Toru KomatsuTetsuo Nagano
May 4, 2007·Organic Letters·Mingjian YuanDaoben Zhu
Mar 22, 2008·ACS Chemical Biology·Luke D Lavis, Ronald T Raines
Dec 9, 2008·Accounts of Chemical Research·Milan Kivala, François Diederich
Dec 24, 2008·Optics Express·Wilfried G J H M van SarkDaniel Vanmaekelbergh
Dec 22, 2009·Physical Chemistry Chemical Physics : PCCP·Yuen Yap ChengTimothy W Schmidt
May 18, 2010·Journal of Fluorescence·Tesfay AtsbehaMesfin Redi-Abshiro
Sep 8, 2010·Chemical Society Reviews·Pavel AnzenbacherMaria E Kozelkova
Nov 26, 2010·Journal of the American Chemical Society·Yuichiro UenoKevin Burgess
Jul 30, 2011·Chemical Society Reviews·Yuning HongBen Zhong Tang
Oct 25, 2011·Angewandte Chemie·Juan F AranedaRobert McDonald
Feb 4, 2012·The Journal of Organic Chemistry·Wade C W LeuC Scott Hartley
Apr 11, 2012·Journal of the American Chemical Society·Daria M ShcherbakovaVladislav V Verkhusha
Oct 31, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Takuhiro TaniguchiShigehiro Yamaguchi
Feb 15, 2014·Journal of the American Chemical Society·Xumeng WuWeihong Zhu
Jul 30, 2014·PloS One·Alexander V FoninKonstantin K Turoverov
Aug 1, 2014·Chemical Communications : Chem Comm·Brandon E HirschAmar H Flood
Jan 15, 2015·The Journal of Physical Chemistry. B·Jiaxing LinDavid N Beratan
Feb 19, 2015·Biophysical Journal·Hylkje J GeertsemaAntoine M van Oijen
Jul 15, 2015·Journal of the American Chemical Society·Masahiro YamashinaMichito Yoshizawa
Aug 14, 2015·Chemical Reviews·Frank WürthnerDavid Schmidt
Oct 28, 2015·Chemical Society Reviews·Vikas S Padalkar, Shu Seki
Mar 26, 2016·Journal of the American Chemical Society·Yun LiuAmar H Flood
Jun 23, 2016·Chemical Communications : Chem Comm·Bo QiaoAmar H Flood
Oct 30, 2016·Angewandte Chemie·Elisabeth M FatilaAmar H Flood
Nov 5, 2016·Chemical Communications : Chem Comm·Bo QiaoAmar H Flood
Dec 20, 2016·Accounts of Chemical Research·James L BanalWallace W H Wong
May 6, 2017·Angewandte Chemie·Ke Min ChanEric T Kool
Jun 2, 2017·Chemistry : a European Journal·Elisabeth M FatilaAmar H Flood

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Citations

Mar 30, 2021·Chemistry : a European Journal·Saber MirzaeiRaúl Hernández Sánchez
Dec 18, 2020·Organic Letters·Edison CastroRaúl Hernández Sánchez

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