Synthesis, Crystal Structure and Photoluminescent Properties of Novel 9-Cyano-Pyrrolo[1,2-a][1,10]Phenanthrolines

Mihaela Cristea; Mihai Răducă; Sergiu Shova; Constantin Drăghici; Vlad A. Neacșu; Maria Maganu; Loredana Albotă (Barbu); Denisa Dumitrescu; Florea Dumitrascu

doi:10.3390/cryst14010067

Synthesis, Crystal Structure and Photoluminescent Properties of Novel 9-Cyano-Pyrrolo[1,2-a][1,10]Phenanthrolines

Mihaela Cristea, Mihai Răducă^*, Sergiu Shova, Constantin Drăghici, Vlad A. Neacșu, Maria Maganu, Loredana Albotă (Barbu), Denisa Dumitrescu, Florea Dumitrascu^*

^*Corresponding author for this work

Department of Chemistry

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

3 Citations (Scopus)

23 Downloads (CityUHK Scholars)

Abstract

Novel 9-cyano-pyrrolo[1,2-a][1,10]phenanthrolines 6a–d were obtained by an efficient one-pot regioselective reaction between 1,10-phenanthrolinium bromides 2a–d and acrylonitrile as a dipolarophile, in the presence of triethylamine and tetrakis-pyridino-cobalt(II) dichromate (TPCD) as oxidizing agents. The optical properties of the compounds were investigated through UV–Vis spectrophotometry and steady-state photoluminescence measurements, while their structures were elucidated by single-crystal X-ray diffraction. The structural characterization revealed that the molecular structures of the four compounds were stabilized by hydrogen bonds and π–π interactions. © 2024 by the authors.

Original language	English
Article number	67
Journal	Crystals
Volume	14
Issue number	1
Online published	7 Jan 2024
DOIs	https://doi.org/10.3390/cryst14010067
Publication status	Published - Jan 2024

Funding

This research received no external funding

Research Keywords

1,10-phenanthrolinium N-ylide
1,3-dipolar cycloaddition
helical chirality
pyrrolo[1,2-a][1,10]phenanthrolines
X-ray diffraction

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title = "Synthesis, Crystal Structure and Photoluminescent Properties of Novel 9-Cyano-Pyrrolo[1,2-a][1,10]Phenanthrolines",

abstract = "Novel 9-cyano-pyrrolo[1,2-a][1,10]phenanthrolines 6a–d were obtained by an efficient one-pot regioselective reaction between 1,10-phenanthrolinium bromides 2a–d and acrylonitrile as a dipolarophile, in the presence of triethylamine and tetrakis-pyridino-cobalt(II) dichromate (TPCD) as oxidizing agents. The optical properties of the compounds were investigated through UV–Vis spectrophotometry and steady-state photoluminescence measurements, while their structures were elucidated by single-crystal X-ray diffraction. The structural characterization revealed that the molecular structures of the four compounds were stabilized by hydrogen bonds and π–π interactions. {\textcopyright} 2024 by the authors.",

keywords = "1,10-phenanthrolinium N-ylide, 1,3-dipolar cycloaddition, helical chirality, pyrrolo[1,2-a][1,10]phenanthrolines, X-ray diffraction",

author = "Mihaela Cristea and Mihai R{\u a}duc{\u a} and Sergiu Shova and Constantin Dr{\u a}ghici and Neacșu, {Vlad A.} and Maria Maganu and {Albot{\u a} (Barbu)}, Loredana and Denisa Dumitrescu and Florea Dumitrascu",

year = "2024",

month = jan,

doi = "10.3390/cryst14010067",

language = "English",

volume = "14",

journal = "Crystals",

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TY - JOUR

T1 - Synthesis, Crystal Structure and Photoluminescent Properties of Novel 9-Cyano-Pyrrolo[1,2-a][1,10]Phenanthrolines

AU - Cristea, Mihaela

AU - Răducă, Mihai

AU - Shova, Sergiu

AU - Drăghici, Constantin

AU - Neacșu, Vlad A.

AU - Maganu, Maria

AU - Albotă (Barbu), Loredana

AU - Dumitrescu, Denisa

AU - Dumitrascu, Florea

PY - 2024/1

Y1 - 2024/1

N2 - Novel 9-cyano-pyrrolo[1,2-a][1,10]phenanthrolines 6a–d were obtained by an efficient one-pot regioselective reaction between 1,10-phenanthrolinium bromides 2a–d and acrylonitrile as a dipolarophile, in the presence of triethylamine and tetrakis-pyridino-cobalt(II) dichromate (TPCD) as oxidizing agents. The optical properties of the compounds were investigated through UV–Vis spectrophotometry and steady-state photoluminescence measurements, while their structures were elucidated by single-crystal X-ray diffraction. The structural characterization revealed that the molecular structures of the four compounds were stabilized by hydrogen bonds and π–π interactions. © 2024 by the authors.

AB - Novel 9-cyano-pyrrolo[1,2-a][1,10]phenanthrolines 6a–d were obtained by an efficient one-pot regioselective reaction between 1,10-phenanthrolinium bromides 2a–d and acrylonitrile as a dipolarophile, in the presence of triethylamine and tetrakis-pyridino-cobalt(II) dichromate (TPCD) as oxidizing agents. The optical properties of the compounds were investigated through UV–Vis spectrophotometry and steady-state photoluminescence measurements, while their structures were elucidated by single-crystal X-ray diffraction. The structural characterization revealed that the molecular structures of the four compounds were stabilized by hydrogen bonds and π–π interactions. © 2024 by the authors.

KW - 1,10-phenanthrolinium N-ylide

KW - 1,3-dipolar cycloaddition

KW - helical chirality

KW - pyrrolo[1,2-a][1,10]phenanthrolines

KW - X-ray diffraction

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U2 - 10.3390/cryst14010067

DO - 10.3390/cryst14010067

M3 - RGC 21 - Publication in refereed journal

SN - 2073-4352

VL - 14

JO - Crystals

JF - Crystals

IS - 1

M1 - 67

ER -

Synthesis, Crystal Structure and Photoluminescent Properties of Novel 9-Cyano-Pyrrolo[1,2-a][1,10]Phenanthrolines

Abstract

Funding

Research Keywords

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