Fluorescence Quenching of Carbonyl-Twisted 5-Acyl-1-dimethylaminonaphthalenes by Alcohols

被引:7
作者
Anderson, Rachel S. [1 ]
Nagirimadugu, Newton, V [1 ]
Abelt, Christopher J. [1 ]
机构
[1] Coll William & Mary, Dept Chem, Williamsburg, VA 23185 USA
基金
美国国家科学基金会;
关键词
PRODAN; SCALE;
D O I
10.1021/acsomega.9b01905
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Derivatives of 1-dimethylamino-5-propionylnaphthalene that constrain the carbonyl group into a five-, six-, and seven-membered ring were prepared, and their fluorescence quenching in protic solvents was studied. Evidence for enhanced quenching due to carbonyl twisting out of the molecular plane is presented, but this effect is heavily masked by the strong quenching by all of the derivatives and by the ring size-dependent deactivation seen in polar, aprotic solvents. Calculations show strong, ring size-dependent vibrational coupling between the carbonyl group and the naphthalene ring in the first excited state.
引用
收藏
页码:14067 / 14073
页数:7
相关论文
共 18 条
[1]   Intramolecular Hydrogen-Bonding Effects on the Fluorescence of PRODAN Derivatives [J].
Alty, Isaac G. ;
Cheek, Douglas W. ;
Chen, Tao ;
Smith, David B. ;
Walhout, Emma Q. ;
Abelt, Christopher J. .
JOURNAL OF PHYSICAL CHEMISTRY A, 2016, 120 (20) :3518-3523
[2]   Synthesis and Photophysical Properties of a Series of Cyclopenta[b]naphthalene Solvatochromic Fluorophores [J].
Benedetti, Erica ;
Kocsis, Laura S. ;
Brummond, Kay M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) :12418-12421
[3]   Intramolecular Didehydro-Diels-Alder Reaction and Its Impact on the Structure-Function Properties of Environmentally Sensitive Fluorophores [J].
Brummond, Kay M. ;
Kocsis, Laura S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (08) :2320-2329
[4]  
Catalan J, 1997, LIEBIGS ANN-RECL, P1941
[5]  
Catalan J, 1991, J Fluoresc, V1, P215, DOI 10.1007/BF00865246
[6]   Toward a Generalized Treatment of the Solvent Effect Based on Four Empirical Scales: Dipolarity (SdP, a New Scale), Polarizability (SP), Acidity (SA), and Basicity (SB) of the Medium [J].
Catalan, Javier .
JOURNAL OF PHYSICAL CHEMISTRY B, 2009, 113 (17) :5951-5960
[7]   1,5-Prodan Emits from a Planar Intramolecular Charge-Transfer Excited State [J].
Chen, Tao ;
Lee, Samuel W. ;
Abelt, Christopher J. .
ACS OMEGA, 2018, 3 (05) :4816-4823
[8]   Does PRODAN Possess an O-TICT Excited State? Synthesis and Properties of Two Constrained Derivatives [J].
Everett, Renata K. ;
Nguyen, A. Ashley ;
Abelt, Christopher J. .
JOURNAL OF PHYSICAL CHEMISTRY A, 2010, 114 (14) :4946-4950
[9]  
Frisch M., 2016, GAUSSIAN 16 VERSION
[10]   Carbonyl-Twisted 6-Acyl-2-dialkylaminonaphthalenes as Solvent Acidity Sensors [J].
Green, Amy M. ;
Naughton, Hannah R. ;
Nealy, Zachariah B. ;
Pike, Robert D. ;
Abelt, Christopher J. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (05) :1784-1789