An NIR-emitting lysosome-targeting probe with large Stokes shift via coupling cyanine and excited-state intramolecular proton transfer

Dahal, Dipendra; McDonald, Lucas; Bi, Xiaoman; Abeywickrama, Chathura S.; Gombedza, Farai; Konopka, Michael; Paruchuri, Sailaja; Pang, Yi

doi:10.1039/c7cc00700k

Cited by 134 publications

(121 citation statements)

References 27 publications

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“…In fact, the interest to the ESIPT process is not limited to academic field. In view of the unique characteristic of dual emission bands, the broad‐scale applications about ESIPT compounds have been heated up, such as photostabilizers, fluorescent sensors, organic light‐emitting diodes (OLEDs), optoelectronics, and so forth …”

Section: Introductionmentioning

confidence: 99%

A detailed theoretical simulation about the excited state dynamical process for the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol molecule

Zhang

Cheng

et al. 2019

J of Physical Organic Chem

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Given that molecular excited state dynamical process plays important roles in designing and developing novel applications in recent years. In this work, based on density functional theory (DFT) and time‐dependent density functional theory (TDDFT) methods, we theoretically explored the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol (HBT‐Cz) system about its excited state behaviors. Via simulating the electrostatic potential surface (EPS) of HBT‐Cz structure, we confirm the formation of intramolecular hydrogen bond O2—H3···N4 in the S0 state. Our theoretical dominating bond lengths, bond angles, and the infrared (IR) vibrational spectra involved in hydrogen bond demonstrate that O2—H3···N4 should be strengthened in the S1 state. Upon the photoexcitation, we find the charge transfer characteristics around hydrogen bonding moieties play important roles in facilitating excited state intramolecular proton transfer (ESIPT) process. Via constructing potential energy curves, we confirm the ESIPT reaction that further explains previous experimental phenomenon. Moreover, we also search the S1‐state transition state (TS) structure along with ESIPT path, based on which we simulate the intrinsic reaction coordinate (IRC) path. Combing with the atom‐centered density matrix propagation (ADMP) molecular dynamics simulation, we further confirm the ESIPT mechanism presented in this work. We sincerely hope that our theoretical work could guide novel applications based on HBT‐Cz system in future.

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Section: Introductionmentioning

confidence: 99%

A detailed theoretical simulation about the excited state dynamical process for the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol molecule

Zhang

Cheng

et al. 2019

J of Physical Organic Chem

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“…Small organic fluorophores are indispensible tools for the construction of fluorescent probes because of the controllable optical properties such as bodipy, coumarin, rhodamine, fluorescein, etc . Among them, fluorophores derived from benzothiazole are widely used as the dye platform for designing of fluorescent probes . In our previous work, a ratiometric fluorescent probe HBT‐FA for sensing formaldehyde based on intramolecular charge transfer (ICT) mechanism by using aza‐cope reaction was constructed, which showed good ratio signals in aqueous and calf serums .…”

Section: Introductionmentioning

confidence: 99%

A Light‐Up Fluorescent Probe for Detection of Formaldehyde in Serum and Gaseous Based on d‐PeT Process

et al. 2019

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A new Light‐Up fluorescent probe (FA‐P) for detection of formaldehyde was designed and synthesized based on the donor‐excited photo induced electron transfer (d‐PeT) process. The probe FA‐P was constructed by integrating a benzothiazole derivatives as the fluorescent skeleton and homoallylamino group as the specific recognition site. It showed the unique advantages of easy‐preparation, and excellent selectivity response toward formaldehyde. Besides, The probe FA‐P can not only detect formaldehyde gas through the prepared test paper, but also detect formaldehyde in serum solution.

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“…And generally, this kind of significant Stokes shift could be as large as 6000 to 12 000 cm −1 . The development of novel materials for chemical sensing, optoelectronics, cell imaging, white LEDs, molecular switches, and so forth was because of this kind of property …”

Section: Introductionmentioning

confidence: 99%

Investigation on the excited state intramolecular proton transfer process for the novel 2‐(3,5‐dichloro‐2‐hydroxy‐phenyl)‐benzooxazole‐5‐carboxylicacid system

Gao

Yang

Zhang

et al. 2019

J of Physical Organic Chem

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In view of the importance of excited state hydrogen bonding interactions and excited state proton transfer (ESPT) dynamical behaviors, in this work, we theoretically explore the excited state process for a novel 2‐(3,5‐dichloro‐2‐hydroxy‐phenyl)‐benzooxazole‐5‐carboxylicacid (DHPBC) system. On the basis of discrete Fourier transform (DFT) and time‐dependent density functional theory (TDDFT) methods, we reappear previous experimental reports with checking the reasonability of our theoretical level. We calculate and compare the primary geometrical parameters and hydrogen bonding energies around hydrogen bonding moieties, which reveals that the intramolecular hydrogen bond OH···N of DHPBC is enhanced in the S1 state. The increased electron densities around N atom contribute to attracting proton of hydroxyl upon the photoexcitation, which plays important roles in strengthening hydrogen bond and in facilitating excited state intra‐ or intermolecular proton transfer (ESIPT) process. Via constructing potential energy curves along with the ESIPT path, we verify that the ESIPT process of DHPBC system is ultrafast because of the low potential energy barrier. That should be the reason why the normal emission of DHPBC cannot be detected in previous experiment. This work not only clarifies the excited state hydrogen bonding interactions and fills the vacancy of specific ESIPT mechanism for DHPBC system in experiment, but also explains the fluorescence quenching phenomenon.

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An NIR-emitting lysosome-targeting probe with large Stokes shift via coupling cyanine and excited-state intramolecular proton transfer

Cited by 134 publications

References 27 publications

A detailed theoretical simulation about the excited state dynamical process for the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol molecule

A detailed theoretical simulation about the excited state dynamical process for the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol molecule

A Light‐Up Fluorescent Probe for Detection of Formaldehyde in Serum and Gaseous Based on d‐PeT Process

Investigation on the excited state intramolecular proton transfer process for the novel 2‐(3,5‐dichloro‐2‐hydroxy‐phenyl)‐benzooxazole‐5‐carboxylicacid system

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