ESIPT or not ESIPT? Revisiting recent results on 2,1,3-benzothiadiazole under the TD-DFT light

被引：34

作者：

Laurent, Adele D. ^{[1
]}

Houari, Ymene ^{[1
]}

Carvalho, Pedro H. P. R. ^{[2
]}

Neto, Brenno A. D. ^{[2
]}

Jacquemin, Denis ^{[1
,3
]}

机构：

[1] Univ Nantes, CEISAM, UMR CNRS 6230, F-44322 Nantes 3, France

[2] Univ Brasilia IQ UnB, Lab Med & Technol Chem, BR-70904970 Brasilia, DF, Brazil

[3] Inst Univ France, F-75005 Paris 5, France

来源：

RSC ADVANCES | 2014年 / 4卷 / 27期

基金：

欧洲研究理事会;

关键词：

INTRAMOLECULAR PROTON-TRANSFER; TRANSFER EXCITED-STATES; FLUORESCENT-PROBES; LUMINESCENCE; PHOTOPHYSICS; CHROMOPHORE; SOLVENT; SENSOR; TDDFT;

D O I：

10.1039/c4ra00991f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Recently, the spectroscopic signatures of amino-substituted benzothiadiazoles were investigated by complementary experimental and theoretical approaches [Neto et al., RSC Adv., 2012, 2, 1524-1532]. It was concluded that these molecules were exhibiting excited-state intramolecular proton transfer. In this communication, we revisit these results using a state-of-the-art time-dependent density functional theory approach which provides a complete explanation to the spectroscopic observations.

引用

页码：14189 / 14192

页数：4

共 31 条

[1] Solvent-dependent photoinduced tautomerization of 2-(2′-hydroxyphenyl)benzoxazole [J].

Abou-Zied, OK ;

Jimenez, R ;

Thompson, EHZ ;

Millar, DP ;

Romesberg, FE .

JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (15) :3665-3672

[2] Excited-state intramolecular proton transfer:: A survey of TDDFT and RI-CC2 excited-state potential energy surfaces [J].

Aquino, AJA ;

Lischka, H ;

Hättig, C .

JOURNAL OF PHYSICAL CHEMISTRY A, 2005, 109 (14) :3201-3208

[3] Ultrafast internal conversion pathway and mechanism in 2-(2′-hydroxyphenyl) benzothiazole: a case study for excited-state intramolecular proton transfer systems [J].

Barbatti, Mario ;

Aquino, Adelia J. A. ;

Lischka, Hans ;

Schriever, Christian ;

Lochbrunner, Stefan ;

Riedle, Eberhard .

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2009, 11 (09) :1406-1415

[4]

Bell R. P., 1973, PROTON TRANSFER CHEM

[5] Ortho green fluorescence protein synthetic chromophore; Excited-state intramolecular proton transfer via a seven-membered-ring hydrogen-bonding system [J].

Chen, Kew-Yu ;

Cheng, Yi-Ming ;

Lai, Cheng-Hsuan ;

Hsu, Cheng-Chih ;

Ho, Mei-Lin ;

Lee, Gene-Hsiang ;

Chou, Pi-Tai .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (15) :4534-+

[6] Excited-state intramolecular proton transfer in 2-(2′,6′-dihydroxyphenyl) benzoxazole: effect of dual hydrogen bonding on the optical properties [J].

Chen, Wei-Hua ;

Pang, Yi .

TETRAHEDRON LETTERS, 2010, 51 (14) :1914-1918

[7] Intramolecular Hydrogen Bonding Plays a Crucial Role in the Photophysics and Photochemistry of the GFP Chromophore [J].

Cui, Ganglong ;

Lan, Zhenggang ;

Thiel, Walter .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (03) :1662-1672

[8] Failure of time-dependent density functional theory for long-range charge-transfer excited states: The zincbacteriochlorin-bacterlochlorin and bacteriochlorophyll-spheroidene complexes [J].

Dreuw, A ;

Head-Gordon, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) :4007-4016

[9] Probing the intramolecular hydrogen bond of 2-(2-hydroxyphenyl)benzotriazoles in polar environment: A photophysical study of UV absorber efficiency [J].

Fluegge, Anja P. ;

Waiblinger, Frank ;

Stein, Martin ;

Keck, Juergen ;

Kramer, Horst E. A. ;

Fischer, Peter ;

Wood, Mervin G. ;

DeBellis, Anthony D. ;

Ravichandran, Ramanathan ;

Leppard, David .

JOURNAL OF PHYSICAL CHEMISTRY A, 2007, 111 (39) :9733-9744

[10] Role of Solvent, pH, and Molecular Size in Excited-State Deactivation of Key Eumelanin Building Blocks: Implications for Melanin Pigment Photostability [J].

Gauden, M. ;

Pezzella, A. ;

Panzella, L. ;

Neves-Petersen, M. T. ;

Skovsen, E. ;

Petersen, S. B. ;

Mullen, K. M. ;

Napolitano, A. ;

d'Ischia, M. ;

Sundstroem, V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (50) :17038-17043

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