2,7-bis(1H-pyrrol-2-yl)ethynyl-1,8-naphthyridine:: An ultrasensitive fluorescent probe for glucopyranoside

被引：56
|
作者：
Liao, JH
Chen, CT [1 ]
Chou, HC
Cheng, CC
Chou, PT
Fang, JM
Slanina, Z
Chow, TJ
机构：
[1] Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan
[2] Acad Sinica, Inst Chem, Nankang 115, Taiwan
来源：
ORGANIC LETTERS | 2002年 / 4卷 / 18期
关键词：
D O I：
10.1021/ol0264096
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] A push-pull conjugated molecule, 2,7-bis(1H-pyrrol-2-yl)ethynyl-1,8-naphthyridine (BPN), has been designed to bind selectively with octyl glucopyranoside (OGU). The BPN/OGU quadruple hydrogen-bonding complex adopts a rigid BPN conformation in which the proton donor (d) and acceptor (a) relays (daad) are resonantly conjugated through the ethynyl bridge, inducing pi-electron delocalization, i.e., a charge transfer effect. The excellent photophysical properties make BPN a highly sensitive probe for monitoring glucopyranoside to a detection limit of similar to100 pM.
引用
收藏
页码：3107 / 3110
页数：4
相关论文
共 50 条
  • [21] 2-Methyl-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline
    Su, Bi-yun
    Qin, Wen-Long
    Jiao, Long
    Wang, Jia-Xiang
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O3326 - +
  • [22] (E)-Ethyl 2-cyano-3-(1H-pyrrol-2-yl)-acrylate
    Yuvaraj, Haldorai
    Gayathri, D.
    Kalkhambkar, Rajesh G.
    Gupta, Vivek K.
    Rajnikant
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2135 - U1410
  • [23] SOME DERIVATIVES OF 1,8-NAPHTHYRIDINE, 1,2-DIHYDROPYRIDO[2,3-B] [1,8]-NAPHTHYRIDINE AND 2H-PYRANO[2,3-B][1,8]NAPHTHYRIDINE
    HENRY, RA
    HAMMOND, PR
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (06) : 1109 - 1114
  • [24] ADDUCTS OF TUNGSTEN-OXIDE TETRAFLUORIDE WITH 1,8-NAPHTHYRIDINE AND 2,7-DIMETHYL-1,8-NAPHTHYRIDINE - PREPARATION AND CHARACTERIZATION OF WOF4.NAPY AND WOF4.DMNAPY
    ARNAUDET, L
    BOUGON, R
    BAN, B
    LANCE, M
    KASKA, WC
    JOURNAL OF FLUORINE CHEMISTRY, 1991, 53 (02) : 171 - 180
  • [25] Crystal structure and Hirshfeld surface analysis of 3-benzyl-2-[bis(1H-pyrrol-2-yl)methyl]thiophene
    Sadikhov, Nurlana D.
    Atioglu, Zeliha
    Guliyeva, Narmina A.
    Shelukho, Evgeniya R.
    Polyanskaya, Darya K.
    Khrustalev, Victor N.
    Akkurt, Mehmet
    Bhattarai, Ajaya
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2024, 80 : 72 - +
  • [26] β-Furan-Fused bis(Difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine Fluorescent Dyes in the Visible Deep-Red Region
    Zhou, Lin
    Xu, Defang
    Gao, Huaizhi
    Zhang, Chao
    Ni, Fangfang
    Zhao, Wenqi
    Cheng, Dandan
    Liu, Xingliang
    Han, Aixia
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (17): : 7439 - 7447
  • [27] 2,5-Dimethyl-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline
    Su, Bi-Yun
    Qin, Wen-Long
    Wang, Jia-Xiang
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O3088 - +
  • [28] 2,3-Dimethyl-N-[(E)-(1H-pyrrol-2-yl)methylidene]aniline
    Tahir, M. Nawaz
    Tariq, Muhammad Ilyas
    Ahmad, Shahbaz
    Sarfraz, Muhammad
    Tariq, Riaz H.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O2295 - U225
  • [29] 1-Amino-6-chloro-2-(1H-pyrrol-2-yl)benzimidazole (RS 1350)
    Pifferi, A
    Camalli, M
    Silvestri, R
    De Martino, G
    Massa, S
    Artico, M
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2001, 57 : o819 - o821
  • [30] COMPLEXES OF 1,8-NAPHTHYRIDINES .8. COMPLEXES OF 2,7-DIMETHYL-1,8-NAPHTHYRIDINE WITH RARE-EARTH NITRATES
    HENDRICKER, DG
    FOSTER, RJ
    JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1972, 34 (06): : 1949 - +
12345