Fluorescence enhancement of quinolines by protonation

Essi Tervola; Khai Nghi Truong; Jas S. Ward; Arri Priimägi; Kari Rissanen

doi:10.1039/d0ra04691d

Fluorescence enhancement of quinolines by protonation

Essi Tervola, Khai Nghi Truong, Jas S. Ward, Arri Priimägi, Kari Rissanen

Materiaalitiede ja ympäristötekniikka

Tutkimustuotos: Artikkeli › Tieteellinen › vertaisarvioitu

37 Sitaatiot (Scopus)

12 Lataukset (Pure)

Abstrakti

A study of the fluorescence enhancement of isoquinoline, acridine (benzo[b]quinoline) and benzo[h]quinoline is reported with six organic acids of different pKa values. Protonation was found to be an effective tool in the fluorescence enhancement of quinolines. A significant increase in the fluorescence intensity is observed only when strong acids are used, resulting in an over 50-fold increase in fluorescence with trifluoroacetic or benzenesulfonic acid and isoquinoline in a 1.5 : 1 ratio. The benzenesulfonic acid was found to be the most effective in the protonation of the bases despite its higher pKa value compared to trifluoro- and trichloroacetic acid. The X-ray crystal structures of 14 salts reveal the charge-assisted hydrogen bond O⋯N distances to vary very little, from 2.560(2)-2.714(3) Å, with the exception of the isoquinolinium benzenesulfonate where the O⋯N distance of 2.862(7) Å is caused by additional intermolecular interactions in the solid-state.

Alkuperäiskieli	Englanti
Sivut	29385-29393
Sivumäärä	9
Julkaisu	RSC Advances
Vuosikerta	10
Numero	49
DOI - pysyväislinkit	https://doi.org/10.1039/d0ra04691d
Tila	Julkaistu - 12 elok. 2020
OKM-julkaisutyyppi	A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Julkaisufoorumi-taso

Jufo-taso 1

!!ASJC Scopus subject areas

Yleinen kemia
Yleinen kemian tekniikka

Pääsy asiakirjaan

10.1039/d0ra04691dLisenssi: CC BY-NC

Fluorescence enhancement of quinolines 2020
CC BY-NC
Final published version, 1,42 MBLisenssi: CC BY-NC

http://urn.fi/URN:NBN:fi:tuni-202012219058Lisenssi: CC BY-NC

CCDC 2000979: Experimental Crystal Structure Determination
Tervola, E. (Contributor), Truong, K.-N. (Contributor), Ward, J. S. (Contributor), Priimagi, A. (Creator) & Rissanen, K. (Contributor), Cambridge Crystallographic Data Centre, 4 toukok. 2020
DOI - pysyväislinkki: 10.5517/ccdc.csd.cc2555q8
Tietoaineisto: Dataset
CCDC 2000981: Experimental Crystal Structure Determination
Tervola, E. (Contributor), Truong, K.-N. (Contributor), Ward, J. S. (Contributor), Priimagi, A. (Creator) & Rissanen, K. (Contributor), Cambridge Crystallographic Data Centre, 4 toukok. 2020
DOI - pysyväislinkki: 10.5517/ccdc.csd.cc2555sb
Tietoaineisto: Dataset
CCDC 2000988: Experimental Crystal Structure Determination
Tervola, E. (Contributor), Truong, K.-N. (Contributor), Ward, J. S. (Contributor), Priimagi, A. (Creator) & Rissanen, K. (Contributor), Cambridge Crystallographic Data Centre, 4 toukok. 2020
DOI - pysyväislinkki: 10.5517/ccdc.csd.cc25560l
Tietoaineisto: Dataset

Fotoniikka-, robotiikka- ja energiamateriaalien tutkimus – Red Labs
Priimägi, A. (Yhteyshenkilö), Vivo, P. (Yhteyshenkilö) & Nonappa, N. (Yhteyshenkilö)
Materiaalitiede ja ympäristötekniikka
Laitteistot/tilat: Facility

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@article{7c1f3692964c4a20b8a6a6ab38c0e8bb,

title = "Fluorescence enhancement of quinolines by protonation",

abstract = "A study of the fluorescence enhancement of isoquinoline, acridine (benzo[b]quinoline) and benzo[h]quinoline is reported with six organic acids of different pKa values. Protonation was found to be an effective tool in the fluorescence enhancement of quinolines. A significant increase in the fluorescence intensity is observed only when strong acids are used, resulting in an over 50-fold increase in fluorescence with trifluoroacetic or benzenesulfonic acid and isoquinoline in a 1.5 : 1 ratio. The benzenesulfonic acid was found to be the most effective in the protonation of the bases despite its higher pKa value compared to trifluoro- and trichloroacetic acid. The X-ray crystal structures of 14 salts reveal the charge-assisted hydrogen bond O⋯N distances to vary very little, from 2.560(2)-2.714(3) {\AA}, with the exception of the isoquinolinium benzenesulfonate where the O⋯N distance of 2.862(7) {\AA} is caused by additional intermolecular interactions in the solid-state. ",

author = "Essi Tervola and Truong, {Khai Nghi} and Ward, {Jas S.} and Arri Priim{\"a}gi and Kari Rissanen",

note = "Funding Information: We gratefully acknowledge nancial support from the Academy of Finland (KR: grant no. 317259; AP: grant no. 311142) and the University of Jyv{\"a}skyl{\"a}, Finland. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

year = "2020",

month = aug,

day = "12",

doi = "10.1039/d0ra04691d",

language = "English",

volume = "10",

pages = "29385--29393",

journal = "RSC Advances",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

number = "49",

}

TY - JOUR

T1 - Fluorescence enhancement of quinolines by protonation

AU - Tervola, Essi

AU - Truong, Khai Nghi

AU - Ward, Jas S.

AU - Priimägi, Arri

AU - Rissanen, Kari

N1 - Funding Information: We gratefully acknowledge nancial support from the Academy of Finland (KR: grant no. 317259; AP: grant no. 311142) and the University of Jyväskylä, Finland. Publisher Copyright: © The Royal Society of Chemistry. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2020/8/12

Y1 - 2020/8/12

N2 - A study of the fluorescence enhancement of isoquinoline, acridine (benzo[b]quinoline) and benzo[h]quinoline is reported with six organic acids of different pKa values. Protonation was found to be an effective tool in the fluorescence enhancement of quinolines. A significant increase in the fluorescence intensity is observed only when strong acids are used, resulting in an over 50-fold increase in fluorescence with trifluoroacetic or benzenesulfonic acid and isoquinoline in a 1.5 : 1 ratio. The benzenesulfonic acid was found to be the most effective in the protonation of the bases despite its higher pKa value compared to trifluoro- and trichloroacetic acid. The X-ray crystal structures of 14 salts reveal the charge-assisted hydrogen bond O⋯N distances to vary very little, from 2.560(2)-2.714(3) Å, with the exception of the isoquinolinium benzenesulfonate where the O⋯N distance of 2.862(7) Å is caused by additional intermolecular interactions in the solid-state.

AB - A study of the fluorescence enhancement of isoquinoline, acridine (benzo[b]quinoline) and benzo[h]quinoline is reported with six organic acids of different pKa values. Protonation was found to be an effective tool in the fluorescence enhancement of quinolines. A significant increase in the fluorescence intensity is observed only when strong acids are used, resulting in an over 50-fold increase in fluorescence with trifluoroacetic or benzenesulfonic acid and isoquinoline in a 1.5 : 1 ratio. The benzenesulfonic acid was found to be the most effective in the protonation of the bases despite its higher pKa value compared to trifluoro- and trichloroacetic acid. The X-ray crystal structures of 14 salts reveal the charge-assisted hydrogen bond O⋯N distances to vary very little, from 2.560(2)-2.714(3) Å, with the exception of the isoquinolinium benzenesulfonate where the O⋯N distance of 2.862(7) Å is caused by additional intermolecular interactions in the solid-state.

U2 - 10.1039/d0ra04691d

DO - 10.1039/d0ra04691d

M3 - Article

AN - SCOPUS:85091640017

SN - 2046-2069

VL - 10

SP - 29385

EP - 29393

JO - RSC Advances

JF - RSC Advances

IS - 49

ER -

Fluorescence enhancement of quinolines by protonation

Abstrakti

Julkaisufoorumi-taso

!!ASJC Scopus subject areas

Pääsy asiakirjaan

Sormenjälki

Tietoaineistot

CCDC 2000979: Experimental Crystal Structure Determination

CCDC 2000981: Experimental Crystal Structure Determination

CCDC 2000988: Experimental Crystal Structure Determination

Laitteet

Fotoniikka-, robotiikka- ja energiamateriaalien tutkimus – Red Labs

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