2,2-Dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (HBBO) derivative: Towards ratiometric sensing of divalent zinc cations

A dual-emissive fluorophore, HBBODipic, exhibiting an Excited-State Intramolecular Proton Transfer (ESIPT) process is described herein. This dye incorporates an aromatic amine group on the benzofuran side which is functionalized by two picolyl moieties, enabling the observation of a dual fluorescenc...
Ausführliche Beschreibung

Gespeichert in:

Autor*in:	Pariat, Thibault [verfasserIn] Vérité, Pauline M. [verfasserIn] Jacquemin, Denis [verfasserIn] Massue, Julien [verfasserIn] Ulrich, Gilles [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2021

Schlagwörter:	Dyes Fluorescence ESIPT ab initio calculations

Übergeordnetes Werk:	Enthalten in: Dyes and pigments - Amsterdam [u.a.] : Elsevier Science, 1980, 190
Übergeordnetes Werk:	volume:190

DOI / URN:	10.1016/j.dyepig.2021.109338

Katalog-ID:	ELV005909430

Internformat


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245	1	0	\|a 2,2-Dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (HBBO) derivative: Towards ratiometric sensing of divalent zinc cations
264		1	\|c 2021
336			\|a nicht spezifiziert \|b zzz \|2 rdacontent
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520			\|a A dual-emissive fluorophore, HBBODipic, exhibiting an Excited-State Intramolecular Proton Transfer (ESIPT) process is described herein. This dye incorporates an aromatic amine group on the benzofuran side which is functionalized by two picolyl moieties, enabling the observation of a dual fluorescence emission in most solvents. This attractive dual emission is related to the modulation of the pKa* by electronic substitution and has already been applied for generating panchromatic white-emission. In this contribution, we extend the applicability of these HBBO-based dual emitters to the ratiometric detection of substrates, taking advantage of the highly environment-sensitive emission profile of the dye, the E/K intensity ratio being strongly tunable. The presence of a dipicolylamino Zn2+-sensitive chelate on the HBBO π-conjugated core enables a drastic change in the emission spectra upon addition of increasing equivalents of zinc perchlorate. The E/K dual emission slowly shifts to a single K* band, evidencing a decrease of electron density on the benzofuranol site, owing to the chelation of the Zn2+ cation at the dipicolylamino site. The results are rationalized using theoretical calculations.
650		4	\|a Dyes
650		4	\|a Fluorescence
650		4	\|a ESIPT
650		4	\|a ab initio calculations
700	1		\|a Vérité, Pauline M. \|e verfasserin \|4 aut
700	1		\|a Jacquemin, Denis \|e verfasserin \|4 aut
700	1		\|a Massue, Julien \|e verfasserin \|0 (orcid)0000-0002-0629-4949 \|4 aut
700	1		\|a Ulrich, Gilles \|e verfasserin \|4 aut
773	0	8	\|i Enthalten in \|t Dyes and pigments \|d Amsterdam [u.a.] : Elsevier Science, 1980 \|g 190 \|h Online-Ressource \|w (DE-627)306658755 \|w (DE-600)1500382-6 \|w (DE-576)116550910 \|x 0143-7208 \|7 nnns
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912			\|a GBV_ILN_74
912			\|a GBV_ILN_90
912			\|a GBV_ILN_95
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912			\|a GBV_ILN_602
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912			\|a GBV_ILN_2005
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912			\|a GBV_ILN_2011
912			\|a GBV_ILN_2014
912			\|a GBV_ILN_2015
912			\|a GBV_ILN_2020
912			\|a GBV_ILN_2021
912			\|a GBV_ILN_2025
912			\|a GBV_ILN_2027
912			\|a GBV_ILN_2034
912			\|a GBV_ILN_2038
912			\|a GBV_ILN_2044
912			\|a GBV_ILN_2048
912			\|a GBV_ILN_2049
912			\|a GBV_ILN_2050
912			\|a GBV_ILN_2056
912			\|a GBV_ILN_2059
912			\|a GBV_ILN_2061
912			\|a GBV_ILN_2064
912			\|a GBV_ILN_2065
912			\|a GBV_ILN_2068
912			\|a GBV_ILN_2088
912			\|a GBV_ILN_2111
912			\|a GBV_ILN_2112
912			\|a GBV_ILN_2113
912			\|a GBV_ILN_2118
912			\|a GBV_ILN_2122
912			\|a GBV_ILN_2129
912			\|a GBV_ILN_2143
912			\|a GBV_ILN_2147
912			\|a GBV_ILN_2148
912			\|a GBV_ILN_2152
912			\|a GBV_ILN_2153
912			\|a GBV_ILN_2190
912			\|a GBV_ILN_2336
912			\|a GBV_ILN_2470
912			\|a GBV_ILN_2507
912			\|a GBV_ILN_2522
912			\|a GBV_ILN_4035
912			\|a GBV_ILN_4037
912			\|a GBV_ILN_4046
912			\|a GBV_ILN_4112
912			\|a GBV_ILN_4125
912			\|a GBV_ILN_4126
912			\|a GBV_ILN_4242
912			\|a GBV_ILN_4251
912			\|a GBV_ILN_4305
912			\|a GBV_ILN_4313
912			\|a GBV_ILN_4322
912			\|a GBV_ILN_4323
912			\|a GBV_ILN_4324
912			\|a GBV_ILN_4326
912			\|a GBV_ILN_4333
912			\|a GBV_ILN_4334
912			\|a GBV_ILN_4335
912			\|a GBV_ILN_4338
912			\|a GBV_ILN_4393
936	b	k	\|a 58.26 \|j Technologie der Farben und Lacke
951			\|a AR
952			\|d 190

Indexfelder

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matchkey_str	article:01437208:2021----::2iioyaiousiue2hdoyezfrnlezxzlhbdrvtvtwrsaim
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publishDate	2021
allfields	10.1016/j.dyepig.2021.109338 doi (DE-627)ELV005909430 (ELSEVIER)S0143-7208(21)00205-9 DE-627 ger DE-627 rda eng 660 DE-600 58.26 bkl Pariat, Thibault verfasserin aut 2,2-Dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (HBBO) derivative: Towards ratiometric sensing of divalent zinc cations 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier A dual-emissive fluorophore, HBBODipic, exhibiting an Excited-State Intramolecular Proton Transfer (ESIPT) process is described herein. This dye incorporates an aromatic amine group on the benzofuran side which is functionalized by two picolyl moieties, enabling the observation of a dual fluorescence emission in most solvents. This attractive dual emission is related to the modulation of the pKa* by electronic substitution and has already been applied for generating panchromatic white-emission. In this contribution, we extend the applicability of these HBBO-based dual emitters to the ratiometric detection of substrates, taking advantage of the highly environment-sensitive emission profile of the dye, the E/K intensity ratio being strongly tunable. The presence of a dipicolylamino Zn2+-sensitive chelate on the HBBO π-conjugated core enables a drastic change in the emission spectra upon addition of increasing equivalents of zinc perchlorate. The E/K dual emission slowly shifts to a single K* band, evidencing a decrease of electron density on the benzofuranol site, owing to the chelation of the Zn2+ cation at the dipicolylamino site. The results are rationalized using theoretical calculations. Dyes Fluorescence ESIPT ab initio calculations Vérité, Pauline M. verfasserin aut Jacquemin, Denis verfasserin aut Massue, Julien verfasserin (orcid)0000-0002-0629-4949 aut Ulrich, Gilles verfasserin aut Enthalten in Dyes and pigments Amsterdam [u.a.] : Elsevier Science, 1980 190 Online-Ressource (DE-627)306658755 (DE-600)1500382-6 (DE-576)116550910 0143-7208 nnns volume:190 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2008 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 58.26 Technologie der Farben und Lacke AR 190
spelling	10.1016/j.dyepig.2021.109338 doi (DE-627)ELV005909430 (ELSEVIER)S0143-7208(21)00205-9 DE-627 ger DE-627 rda eng 660 DE-600 58.26 bkl Pariat, Thibault verfasserin aut 2,2-Dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (HBBO) derivative: Towards ratiometric sensing of divalent zinc cations 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier A dual-emissive fluorophore, HBBODipic, exhibiting an Excited-State Intramolecular Proton Transfer (ESIPT) process is described herein. This dye incorporates an aromatic amine group on the benzofuran side which is functionalized by two picolyl moieties, enabling the observation of a dual fluorescence emission in most solvents. This attractive dual emission is related to the modulation of the pKa* by electronic substitution and has already been applied for generating panchromatic white-emission. In this contribution, we extend the applicability of these HBBO-based dual emitters to the ratiometric detection of substrates, taking advantage of the highly environment-sensitive emission profile of the dye, the E/K intensity ratio being strongly tunable. The presence of a dipicolylamino Zn2+-sensitive chelate on the HBBO π-conjugated core enables a drastic change in the emission spectra upon addition of increasing equivalents of zinc perchlorate. The E/K dual emission slowly shifts to a single K* band, evidencing a decrease of electron density on the benzofuranol site, owing to the chelation of the Zn2+ cation at the dipicolylamino site. The results are rationalized using theoretical calculations. Dyes Fluorescence ESIPT ab initio calculations Vérité, Pauline M. verfasserin aut Jacquemin, Denis verfasserin aut Massue, Julien verfasserin (orcid)0000-0002-0629-4949 aut Ulrich, Gilles verfasserin aut Enthalten in Dyes and pigments Amsterdam [u.a.] : Elsevier Science, 1980 190 Online-Ressource (DE-627)306658755 (DE-600)1500382-6 (DE-576)116550910 0143-7208 nnns volume:190 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2008 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 58.26 Technologie der Farben und Lacke AR 190
allfields_unstemmed	10.1016/j.dyepig.2021.109338 doi (DE-627)ELV005909430 (ELSEVIER)S0143-7208(21)00205-9 DE-627 ger DE-627 rda eng 660 DE-600 58.26 bkl Pariat, Thibault verfasserin aut 2,2-Dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (HBBO) derivative: Towards ratiometric sensing of divalent zinc cations 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier A dual-emissive fluorophore, HBBODipic, exhibiting an Excited-State Intramolecular Proton Transfer (ESIPT) process is described herein. This dye incorporates an aromatic amine group on the benzofuran side which is functionalized by two picolyl moieties, enabling the observation of a dual fluorescence emission in most solvents. This attractive dual emission is related to the modulation of the pKa* by electronic substitution and has already been applied for generating panchromatic white-emission. In this contribution, we extend the applicability of these HBBO-based dual emitters to the ratiometric detection of substrates, taking advantage of the highly environment-sensitive emission profile of the dye, the E/K intensity ratio being strongly tunable. The presence of a dipicolylamino Zn2+-sensitive chelate on the HBBO π-conjugated core enables a drastic change in the emission spectra upon addition of increasing equivalents of zinc perchlorate. The E/K dual emission slowly shifts to a single K* band, evidencing a decrease of electron density on the benzofuranol site, owing to the chelation of the Zn2+ cation at the dipicolylamino site. The results are rationalized using theoretical calculations. Dyes Fluorescence ESIPT ab initio calculations Vérité, Pauline M. verfasserin aut Jacquemin, Denis verfasserin aut Massue, Julien verfasserin (orcid)0000-0002-0629-4949 aut Ulrich, Gilles verfasserin aut Enthalten in Dyes and pigments Amsterdam [u.a.] : Elsevier Science, 1980 190 Online-Ressource (DE-627)306658755 (DE-600)1500382-6 (DE-576)116550910 0143-7208 nnns volume:190 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2008 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 58.26 Technologie der Farben und Lacke AR 190
allfieldsGer	10.1016/j.dyepig.2021.109338 doi (DE-627)ELV005909430 (ELSEVIER)S0143-7208(21)00205-9 DE-627 ger DE-627 rda eng 660 DE-600 58.26 bkl Pariat, Thibault verfasserin aut 2,2-Dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (HBBO) derivative: Towards ratiometric sensing of divalent zinc cations 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier A dual-emissive fluorophore, HBBODipic, exhibiting an Excited-State Intramolecular Proton Transfer (ESIPT) process is described herein. This dye incorporates an aromatic amine group on the benzofuran side which is functionalized by two picolyl moieties, enabling the observation of a dual fluorescence emission in most solvents. This attractive dual emission is related to the modulation of the pKa* by electronic substitution and has already been applied for generating panchromatic white-emission. In this contribution, we extend the applicability of these HBBO-based dual emitters to the ratiometric detection of substrates, taking advantage of the highly environment-sensitive emission profile of the dye, the E/K intensity ratio being strongly tunable. The presence of a dipicolylamino Zn2+-sensitive chelate on the HBBO π-conjugated core enables a drastic change in the emission spectra upon addition of increasing equivalents of zinc perchlorate. The E/K dual emission slowly shifts to a single K* band, evidencing a decrease of electron density on the benzofuranol site, owing to the chelation of the Zn2+ cation at the dipicolylamino site. The results are rationalized using theoretical calculations. Dyes Fluorescence ESIPT ab initio calculations Vérité, Pauline M. verfasserin aut Jacquemin, Denis verfasserin aut Massue, Julien verfasserin (orcid)0000-0002-0629-4949 aut Ulrich, Gilles verfasserin aut Enthalten in Dyes and pigments Amsterdam [u.a.] : Elsevier Science, 1980 190 Online-Ressource (DE-627)306658755 (DE-600)1500382-6 (DE-576)116550910 0143-7208 nnns volume:190 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2008 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 58.26 Technologie der Farben und Lacke AR 190
allfieldsSound	10.1016/j.dyepig.2021.109338 doi (DE-627)ELV005909430 (ELSEVIER)S0143-7208(21)00205-9 DE-627 ger DE-627 rda eng 660 DE-600 58.26 bkl Pariat, Thibault verfasserin aut 2,2-Dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (HBBO) derivative: Towards ratiometric sensing of divalent zinc cations 2021 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier A dual-emissive fluorophore, HBBODipic, exhibiting an Excited-State Intramolecular Proton Transfer (ESIPT) process is described herein. This dye incorporates an aromatic amine group on the benzofuran side which is functionalized by two picolyl moieties, enabling the observation of a dual fluorescence emission in most solvents. This attractive dual emission is related to the modulation of the pKa* by electronic substitution and has already been applied for generating panchromatic white-emission. In this contribution, we extend the applicability of these HBBO-based dual emitters to the ratiometric detection of substrates, taking advantage of the highly environment-sensitive emission profile of the dye, the E/K intensity ratio being strongly tunable. The presence of a dipicolylamino Zn2+-sensitive chelate on the HBBO π-conjugated core enables a drastic change in the emission spectra upon addition of increasing equivalents of zinc perchlorate. The E/K dual emission slowly shifts to a single K* band, evidencing a decrease of electron density on the benzofuranol site, owing to the chelation of the Zn2+ cation at the dipicolylamino site. The results are rationalized using theoretical calculations. Dyes Fluorescence ESIPT ab initio calculations Vérité, Pauline M. verfasserin aut Jacquemin, Denis verfasserin aut Massue, Julien verfasserin (orcid)0000-0002-0629-4949 aut Ulrich, Gilles verfasserin aut Enthalten in Dyes and pigments Amsterdam [u.a.] : Elsevier Science, 1980 190 Online-Ressource (DE-627)306658755 (DE-600)1500382-6 (DE-576)116550910 0143-7208 nnns volume:190 GBV_USEFLAG_U SYSFLAG_U GBV_ELV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_150 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2008 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2027 GBV_ILN_2034 GBV_ILN_2038 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2190 GBV_ILN_2336 GBV_ILN_2470 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 58.26 Technologie der Farben und Lacke AR 190
language	English
source	Enthalten in Dyes and pigments 190 volume:190
sourceStr	Enthalten in Dyes and pigments 190 volume:190
format_phy_str_mv	Article
bklname	Technologie der Farben und Lacke
institution	findex.gbv.de
topic_facet	Dyes Fluorescence ESIPT ab initio calculations
dewey-raw	660
isfreeaccess_bool	false
container_title	Dyes and pigments
authorswithroles_txt_mv	Pariat, Thibault @@aut@@ Vérité, Pauline M. @@aut@@ Jacquemin, Denis @@aut@@ Massue, Julien @@aut@@ Ulrich, Gilles @@aut@@
publishDateDaySort_date	2021-01-01T00:00:00Z
hierarchy_top_id	306658755
dewey-sort	3660
id	ELV005909430
language_de	englisch
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author	Pariat, Thibault
spellingShingle	Pariat, Thibault ddc 660 bkl 58.26 misc Dyes misc Fluorescence misc ESIPT misc ab initio calculations 2,2-Dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (HBBO) derivative: Towards ratiometric sensing of divalent zinc cations
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topic_title	660 DE-600 58.26 bkl 2,2-Dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (HBBO) derivative: Towards ratiometric sensing of divalent zinc cations Dyes Fluorescence ESIPT ab initio calculations
topic	ddc 660 bkl 58.26 misc Dyes misc Fluorescence misc ESIPT misc ab initio calculations
topic_unstemmed	ddc 660 bkl 58.26 misc Dyes misc Fluorescence misc ESIPT misc ab initio calculations
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title	2,2-Dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (HBBO) derivative: Towards ratiometric sensing of divalent zinc cations
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title_full	2,2-Dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (HBBO) derivative: Towards ratiometric sensing of divalent zinc cations
author_sort	Pariat, Thibault
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author_browse	Pariat, Thibault Vérité, Pauline M. Jacquemin, Denis Massue, Julien Ulrich, Gilles
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title_sort	2,2-dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (hbbo) derivative: towards ratiometric sensing of divalent zinc cations
title_auth	2,2-Dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (HBBO) derivative: Towards ratiometric sensing of divalent zinc cations
abstract	A dual-emissive fluorophore, HBBODipic, exhibiting an Excited-State Intramolecular Proton Transfer (ESIPT) process is described herein. This dye incorporates an aromatic amine group on the benzofuran side which is functionalized by two picolyl moieties, enabling the observation of a dual fluorescence emission in most solvents. This attractive dual emission is related to the modulation of the pKa* by electronic substitution and has already been applied for generating panchromatic white-emission. In this contribution, we extend the applicability of these HBBO-based dual emitters to the ratiometric detection of substrates, taking advantage of the highly environment-sensitive emission profile of the dye, the E/K intensity ratio being strongly tunable. The presence of a dipicolylamino Zn2+-sensitive chelate on the HBBO π-conjugated core enables a drastic change in the emission spectra upon addition of increasing equivalents of zinc perchlorate. The E/K dual emission slowly shifts to a single K* band, evidencing a decrease of electron density on the benzofuranol site, owing to the chelation of the Zn2+ cation at the dipicolylamino site. The results are rationalized using theoretical calculations.
abstractGer	A dual-emissive fluorophore, HBBODipic, exhibiting an Excited-State Intramolecular Proton Transfer (ESIPT) process is described herein. This dye incorporates an aromatic amine group on the benzofuran side which is functionalized by two picolyl moieties, enabling the observation of a dual fluorescence emission in most solvents. This attractive dual emission is related to the modulation of the pKa* by electronic substitution and has already been applied for generating panchromatic white-emission. In this contribution, we extend the applicability of these HBBO-based dual emitters to the ratiometric detection of substrates, taking advantage of the highly environment-sensitive emission profile of the dye, the E/K intensity ratio being strongly tunable. The presence of a dipicolylamino Zn2+-sensitive chelate on the HBBO π-conjugated core enables a drastic change in the emission spectra upon addition of increasing equivalents of zinc perchlorate. The E/K dual emission slowly shifts to a single K* band, evidencing a decrease of electron density on the benzofuranol site, owing to the chelation of the Zn2+ cation at the dipicolylamino site. The results are rationalized using theoretical calculations.
abstract_unstemmed	A dual-emissive fluorophore, HBBODipic, exhibiting an Excited-State Intramolecular Proton Transfer (ESIPT) process is described herein. This dye incorporates an aromatic amine group on the benzofuran side which is functionalized by two picolyl moieties, enabling the observation of a dual fluorescence emission in most solvents. This attractive dual emission is related to the modulation of the pKa* by electronic substitution and has already been applied for generating panchromatic white-emission. In this contribution, we extend the applicability of these HBBO-based dual emitters to the ratiometric detection of substrates, taking advantage of the highly environment-sensitive emission profile of the dye, the E/K intensity ratio being strongly tunable. The presence of a dipicolylamino Zn2+-sensitive chelate on the HBBO π-conjugated core enables a drastic change in the emission spectra upon addition of increasing equivalents of zinc perchlorate. The E/K dual emission slowly shifts to a single K* band, evidencing a decrease of electron density on the benzofuranol site, owing to the chelation of the Zn2+ cation at the dipicolylamino site. The results are rationalized using theoretical calculations.
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title_short	2,2-Dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (HBBO) derivative: Towards ratiometric sensing of divalent zinc cations
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author2	Vérité, Pauline M. Jacquemin, Denis Massue, Julien Ulrich, Gilles
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doi_str	10.1016/j.dyepig.2021.109338
up_date	2024-07-06T19:34:46.205Z
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2,2-Dipicolylamino substituted 2-(2′-hydroxybenzofuranyl) benzoxazole (HBBO) derivative: Towards ratiometric sensing of divalent zinc cations

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