Triarylborane‐Triphenylamine Based Donor‐Acceptor Fluorophores as pH and Fluoride Sensors

ChemistrySelectVolume 9, Issue 14 e202305115 Research Article Triarylborane-Triphenylamine Based Donor-Acceptor Fluorophores as pH and Fluoride Sensors Chinna Ayya Swamy P, Corresponding Author Chinna Ayya Swamy P [email protected] Main Group Organometallic Optoelectronic Materials and Catalysis Lab, National Institute of Technology, Department of Chemistry, Calicut, 673601 IndiaSearch for more papers by this authorArchana V. Raveendran, Archana V. Raveendran Main Group Organometallic Optoelectronic Materials and Catalysis Lab, National Institute of Technology, Department of Chemistry, Calicut, 673601 IndiaSearch for more papers by this author Chinna Ayya Swamy P, Corresponding Author Chinna Ayya Swamy P [email protected] Main Group Organometallic Optoelectronic Materials and Catalysis Lab, National Institute of Technology, Department of Chemistry, Calicut, 673601 IndiaSearch for more papers by this authorArchana V. Raveendran, Archana V. Raveendran Main Group Organometallic Optoelectronic Materials and Catalysis Lab, National Institute of Technology, Department of Chemistry, Calicut, 673601 IndiaSearch for more papers by this author First published: 09 April 2024 https://doi.org/10.1002/slct.202305115Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract We have accomplished the synthesis and characterization of three novel TPA-TAB donor-acceptor conjugate which is capable of dual sensing the pH variations as well as fluoride ions. All the molecules show a turn-on response towards acidic pH, which is facilitated by the presence of donor type NMe2 unit, which are capable of protonation due disruption of photoinduced electron transfer (PET). Three novel triarylborane (TAB)-triphenylamine (TPA)-based fluorophores functionalized with an NMe2 moiety capable of sensing acidic pH variations have been developed. The pH sensing ability relies on the phenomenon of PET. Characterization of synthesized molecules 1–3 was conducted using various analytical techniques, and their photophysical properties were investigated. The TAB-TPA conjugates exhibit solvatochromic fluorescence emission, validating their Donor-Acceptor character and indicating an Intramolecular Charge Transfer (ICT) process. UV-Vis and fluorescence spectroscopic studies revealed that compound 2 exhibits bathochromic shifts and larger Stoke's shift values compared to 1 and 3, attributed to the presence of additional donor groups such as two NMe2 units. pH titrations showed a turn-on fluorescence response towards acidic pH for all molecules, with emission properties remaining unaltered under alkaline pH conditions. The sensing mechanism is attributed to protonation of the −NMe2 unit, disabling existing PET and forming new ICT, leading to enhanced emission for all molecules. Additionally, these conjugates demonstrated recognition of fluoride ions due to the empty p-orbital on the boron center, showing similar sensing ability across all conjugates and selective recognition of fluoride ions without interference from other anions. Conflict of interests The authors declare no competing financial interests. Open Research Data Availability Statement The data that support the findings of this study are available from the corresponding author upon reasonable request. Keywords: Triarylborane, Fluoride Sensing, Donor-Acceptor Conjugates, pH Sensing. Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Filename Description slct202305115-sup-0001-misc_information.pdf4.2 MB Supporting Information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. 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