Issue 16, 2018

Tetraphenylethene– and diphenyldibenzofulvene–anthracene-based fluorescence sensors possessing photo-induced electron transfer and aggregation-induced emission enhancement characteristics for detection of water

Abstract

We have designed and developed a tetraphenylethene (TPE)–anthracene–(aminomethyl)-4-cyanophenylboronic acid ester (AminoMeCNPhenylBPin) structure (RS-1) and a diphenyldibenzofulvene (DPDBF)–anthracene–AminoMeCNPhenylBPin structure (RS-2) possessing PET (photo-induced electron transfer) and AIEE (aggregation-induced emission enhancement) characteristics as PET/AIEE hybrid fluorescence sensors for detection of water in the low and high water content regions in solvents, where the TPE or DPDBF unit is directly attached to the 10-position on the anthracene skeleton. For both RS-1 and RS-2 the enhancement of the fluorescence band at around 430 nm in the low water content region below 1.0 wt% is attributed to the fluorescence emission originating from the anthracene skeleton due to the formation of PET inactive species RS-1(H2O) and RS-2(H2O), respectively, upon addition of water molecules. Furthermore, the appearance of new and broad fluorescence bands at around 450 nm for RS-1 and 530 nm for RS-2 in the high water content region of over 60–70 wt% is attributed to the AIEE characteristics due to the restricted intramolecular rotation (RIR) of the TPE or DPDBF unit associated with aggregate formation (RS-1(H2O)-A and RS-2(H2O)-A). It is worth noting that a big difference in the enhancement of the fluorescence band originating from the anthracene skeleton due to the suppression of the PET characteristics and the appearance of a fluorescence band due to the AIEE characteristics with aggregate formation between RS-1 and RS-2 was observed: for RS-2 the separation of fluorescence peak wavelengths originating from the anthracene skeleton (at ∼430 nm) and due to the RIR of the DPDBF unit with the aggregate formation (at ∼530 nm) is clear, but for RS-1 the separation of fluorescence peak wavelengths is completely indistinct. Consequently, this work indicates that RS-2 having a DPDBF unit on the anthracene skeleton can act as a PET/AIEE hybrid-based dual-fluorescence emission sensor for detection of water in the low and high water content regions in solvents.

Graphical abstract: Tetraphenylethene– and diphenyldibenzofulvene–anthracene-based fluorescence sensors possessing photo-induced electron transfer and aggregation-induced emission enhancement characteristics for detection of water

Supplementary files

Article information

Article type
Paper
Submitted
22 May 2018
Accepted
05 Jul 2018
First published
05 Jul 2018

New J. Chem., 2018,42, 13339-13350

Tetraphenylethene– and diphenyldibenzofulvene–anthracene-based fluorescence sensors possessing photo-induced electron transfer and aggregation-induced emission enhancement characteristics for detection of water

Y. Ooyama, R. Sagisaka, T. Enoki, N. Tsunoji and J. Ohshita, New J. Chem., 2018, 42, 13339 DOI: 10.1039/C8NJ02522C

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